Category: 87661-20-9

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H14O2

To a solution of 1M LDA (42.1 mmol, 42.1 mL) at – 78 C was added dropwise t-butylcyclopropane carboxylate (5.0 g, 35.1 mmol) in 70 mL THF. After 1.5 hours, a solution of allyl bromide (3.03 mL, 35.1 mmol) in 10 mL THF was added. The reaction mixture was allowed to warm slowly to room temperature. After 18 hours, the reaction was quenched with saturated NH4CI (aq), and partitioned between EtOAc and H2O. The organic and aqueous layers were separated, and the aqueous layer was washed with 2 c 20 mL ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified on an 80 g silacel column, eluting with 0-15% EtOAc/hexanes. The product fractions were concentrated in vacuo to yield 1-allyl-cyclopropanecarboxylic acid tert-butyl ester, 2.48 g (38% yield). 1H NMR (CHLOROFORM-d) d: 5.73-6.01 (m, 1H), 4.91-5.13 (m, 2H), 2.27 (dt, J=6.6, 1.3 Hz, 2H), 1.42 (s, 9H), 0.99-1.20 (m, 2H), 0.49-0.73 (m, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BIOHAVEN PHARMACEUTICAL HOLDING COMPANY LTD.; CONWAY, Charles M.; DUBOWCHIK, Gene M.; PELLETIER, Jeffery Claude; REITZ, Allen B.; (186 pag.)WO2020/77038; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 87661-20-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 87661-20-9 name is tert-Butyl cyclopropanecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

c) 1 -r(2S,5R)-5-r4-(3-Methoxy-propyl)-2,2-dimethyl-3,4-dihvdro-2H- benzori ,41oxazin-6-ylmethoxy1-1 -(toluene-4-sulfonyl)-piperidin-2-ylmethyl1- cvclopropanecarboxylic acid tert-butyl ester; A solution of 5.00 mmol of cyclopropanecarboxylic acid tert-butyl ester [87661 -20-9] in 50 ml of tetrahydrofuran at -78C is treated with 5.5 mmol of lithium diisopropyl- amine. The reaction mixture is stirred at -78C for 4 hours before the addition of a solution of 6.00 mmol of 6-[(3R,6S)-6-bromomethyl-1 -(toluene-4-sulfonyl)-piperidin-3- yloxymethyl]-4-(3-methoxy-propyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1 ,4]oxazine in 10 ml of tetrahydrofuran. The reaction is stirred at -78C for 1 hour, then allowed to warm to room temperature over 4 hours, and quenched with saturated aqueous ammonium chloride solution. The mixture is extracted with tert butyl-methyl ether (3x), the combined organic extracts are dried with sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound, which is identified based on the Rf value.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl cyclopropanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2009/106599; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H14O2

Example 226Atert-Butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropanecarboxylate; 9.7 ml (24.3 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution, cooled to from -20 C. to -30 C., of 3.4 ml (24.3 mmol) of diisopropylamine in 20 ml of abs. THF. After the addition had ended, the mixture was stirred at from -20 C. to -30 C. for another 30 min. The mixture was then cooled to -78 C., and a solution of 2.53 g (17.8 mmol) of tert-butyl cyclopropanecarboxylate in 15 ml of abs. THF was added dropwise at this temperature. After 4 h at -78 C., a solution of 3 g (16.2 mmol) of 4-chloro-3-nitrobenzaldehyde in 15 ml of abs. THF was then added. The reaction mixture was slowly warmed to RT overnight and then allowed to stand at RT for three days, and saturated aqueous ammonium chloride solution was then added. The mixture was extracted with ethyl acetate and the organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1?20:1). This gave 3.21 g of the target compound (60.6% of theory).LC-MS (Method 2): Rt=2.42 min; m/z=328 (M+H)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.91-1.01 (m, 2H), 1.05-1.12 (m, 1H), 1.14-1.21 (m, 1H), 1.23 (s, 9H), 4.91 (d, 1H), 5.74 (d, 1H), 7.67-7.76 (m, 2H), 8.00 (d, 1H).

According to the analysis of related databases, 87661-20-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 87661-20-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1Atert-Butyl 1-(3-bromobenzyl)cyclopropanecarboxylate; Under argon, 14.8 ml (105.48 mmol) of diisopropylamine were initially charged in 66 ml of dry THF, and the mixture was cooled to -40 C. 42.2 ml (105.48 mmol) of n-butyllithium solution (2.5 M in hexane) were slowly added dropwise and the mixture was stirred for 30 min. The reaction solution was then cooled to -78 C., and a solution of 10.0 g (70.32 mmol) of tert-butyl cyclopropanecarboxylate in 17 ml of THF was added. After 4 h of stirring at -78 C., a solution of 19.34 g (77.36 mmol) of 3-bromobenzyl bromide in 17 ml THF was added. The reaction mixture was slowly warmed to RT overnight, and aqueous ammonium chloride solution was then added carefully and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on 750 g of silica gel (mobile phase cyclohexane/dichloromethane 50:1, then 5:1). This gave 13.3 g (60.7% of theory) of the title compound.GC-MS (Method 1): Rt=5.94 min; m/z=256 (M-C4H8)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=7.46 (s, 1H), 7.38 (m, 1H), 7.25 (m, 2H), 2.82 (s, 2H), 1.28 (s, 9H), 1.08 (q, 2H), 0.87 (q, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1; 4-(l-terf-Butoxycarbonyl-cyclopropyl)-4-hydroxy-piperidine-l-carboxylic acid benzyl ester: To a cooled (-780C) solution of 2.OM lithium dsopropylamide in heptane/ THF/ ethylbenzene (27.4 mL, 54.8 mmol) was added cyclopropanecarboxylic acid terf-butyl ester (7.08 g, 49.8 mmol) in THF (35 mL). After stirring at -780C for 1 h, a solution of 4-oxo-piperidine-l- carboxylic acid benzyl ester (11.6 g, 49.8 mmol) in THF (50 mL) was added. The reaction mixture was stirred at -780C for 3 h then warmed to room temperature. After stirring at ambient temperature for 16 h, the mixture was quenched with saturated aqueous solution of NH4Cl (150 mL) and extracted with EtOAc (150 mL x 3). The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc in Hexane) to yield 4-(l-tert-butoxycarbonyl- cyclopropyl)-4-hydroxy-piperidine-l-carboxylic acid benzyl ester (8.07 g, 43%). 1H NMR (400 MHz, CDCl3) delta 7.36-7.28 (m, 5H), 5.11 (s, 2H), 4.50 (s, IH), 4.00 (bis, 2H), 3.20 (brs, 2H), 1.72- 1.64 (m, 2H), 1.42 (s, 9H), 1.40-1.30 (m, 2H), 1.10 (dd, J=7.0 and 2.4 Hz, 2H), 0.88 (dd, J=7.0 and 2.4 Hz, 2H).

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; PETERSON, John; CHEN, Chien-an; CHEN, Bin; WU, Lingyun; SABIO, Michael; WO2010/53861; (2010); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 87661-20-9, The chemical industry reduces the impact on the environment during synthesis 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, I believe this compound will play a more active role in future production and life.

To a solution of diisopropylamine (24.5 ml) in THF (300 ml) was added at -20 C n-butyllithium (1.6 M solution in hexane, 109 ml), the mixture was warmed to 0C for 30 min and cooled to -78 C. The solution was treated with a solution of cyclopropanecarboxylic acid tert-butyl ester (24.8 g, preparation described in St.W. Wright et al, Tetrahedron Lett. 38, 7345 1997) in THF (50 ml) and after stirring for 4 h at -78C a solution of (R)-2-methyl-propane-2-sulfmic acid [l-(2-fluoro-5-nitro-phenyl)-(E)-ethylidene]- amide (50.0g) in THF (50 ml) was added and stirring was continued for 4 h. The mixture was quenched with brine, extracted with ethyl acetate, the organic layer was dried and evaporated. The residue was purified by chromatography over silica using cyclohexane /ethylacetate (4: 1) to give 1 -[(S)- l-(2-fluoro-5-nitro-phenyl)- 1 -((R)-2-methyl-propane-2-sulfinylamino)-ethyl]- cyclopropanecarboxylic acid tert-butyl ester (17.3 g) as a pale brown oil. MS (ESI): m/z = 429.3 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BANNER, David; HILPERT, Hans; MAUSER, Harald; MAYWEG, Alexander V.; ROGERS-EVANS, Mark; WO2011/70029; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 87661-20-9,Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 193A(+/-)-tert-Butyl 1-[(3-bromo-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate; 42.2 ml (105.5 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution, cooled to from -20 C. to -30 C., of 14.8 ml (105.5 mmol) of diisopropylamine in 60 ml of abs. THF. After the addition had ended, the mixture was stirred at from -20 C. to -30 C. for another 30 min. The mixture was then cooled to -78 C., and a solution of 12.0 g (84.4 mmol) of tert-butyl cyclopropanecarboxylate in 60 ml of abs. THF was added dropwise at this temperature. After 4 h at -78 C., a solution of 15.4 g (70.3 mmol) of 3-bromo-4-chlorobenzaldehyde in 60 ml of abs. THF was added. The reaction mixture was slowly warmed to RT overnight, saturated aqueous ammonium chloride solution was then added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1?10:1). This gave 16.2 g of the target compound (52.5% of theory).LC-MS (Method 4): Rt=1.47 min; m/z=286/288.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.84-0.99 (m, 2H), 1.02-1.17 (m, 2H), 1.24 (s, 9H), 4.88 (d, 1H), 5.55 (d, 1H), 7.39 (dd, 1H), 7.57 (d, 1H), 7.71 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl cyclopropanecarboxylate, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 87661-20-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 87661-20-9 name is tert-Butyl cyclopropanecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

c) 1 -r(2S,5R)-5-r4-(3-Methoxy-propyl)-2,2-dimethyl-3,4-dihvdro-2H- benzori ,41oxazin-6-ylmethoxy1-1 -(toluene-4-sulfonyl)-piperidin-2-ylmethyl1- cvclopropanecarboxylic acid tert-butyl ester; A solution of 5.00 mmol of cyclopropanecarboxylic acid tert-butyl ester [87661 -20-9] in 50 ml of tetrahydrofuran at -78C is treated with 5.5 mmol of lithium diisopropyl- amine. The reaction mixture is stirred at -78C for 4 hours before the addition of a solution of 6.00 mmol of 6-[(3R,6S)-6-bromomethyl-1 -(toluene-4-sulfonyl)-piperidin-3- yloxymethyl]-4-(3-methoxy-propyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1 ,4]oxazine in 10 ml of tetrahydrofuran. The reaction is stirred at -78C for 1 hour, then allowed to warm to room temperature over 4 hours, and quenched with saturated aqueous ammonium chloride solution. The mixture is extracted with tert butyl-methyl ether (3x), the combined organic extracts are dried with sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound, which is identified based on the Rf value.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl cyclopropanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2009/106599; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 87661-20-9, The chemical industry reduces the impact on the environment during synthesis 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, I believe this compound will play a more active role in future production and life.

tert-Butyl 1-allylcyclopropanecarboxylate STR11 A solution of 34.1 g (0.24 mol) of tert-butyl cyclopropanecarboxylate in 25 ml of tetrahydrofuran was added dropwise at -70 C. to a mixture of 33.6 ml (0.24 mol) of diisopropylamine, 150 ml of a 1.5 molar solution of n-butyllithium in n-hexane (=0.24 mol of butyllithium) and 100 ml of tetrahydrofuran. Stirring was carried out for 3 hours at -70 C., after which a solution of 27.8 g (0.23 mol) of allyl bromide in 25 ml of tetrahydrofuran was added dropwise. Thereafter, the reaction mixture was stirred for a further 2 hours at -70 C. and then for 12 hours at 20 C. After hydrolysis with 50 ml of saturated aqueous ammonium chloride solution and after phase separation, the organic phase was worked up in a conventional manner to obtain the product. The crude product was purified by distillation. Yield: 61%, bp.: 86-88 C. at 30 mbar; colorless oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF Aktiengesellschaft; US5371268; (1994); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H14O2

Example 71 (2S)-1-{1-[2-(4-Fluoro-3-methyl-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile The title compound was prepared in analogy to example 60, steps A] to C] starting from 4-chloromethyl-5-methyl-2-(4-fluoro-3-methyl-phenyl)-oxazole and tert.butyl cyclopropanecarboxylate. The starting material could be prepared from 4-fluoro-3-methylbenzaldehyde and 2,3-butanedione oxime as described for benzaldehyde in Chem. Pharm. Bull. 1971, 19, 2050-2057. The title compound was obtained as a white gum. MS (ISP): 397.3 (MH+).

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer, Markus; Hunziker, Daniel; Kuehne, Holger; Loeffler, Bernd M.; Sarabu, Ramakanth; Wessel, Hans P.; US2003/130281; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics