Category: 3697-68-5

3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate

To a solution of Preparation 232 1-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (3.00 g, 21.00 mmol) in dichloromethane (50 ml), at 0 C., was added saturated sodium hydrogen carbonate solution (50 ml), followed by TEMPO (659 mg, 4.00 mmol) and sodium bromide (400 mg, 4.00 mmol). After stirring for 5 min, sodium hypochlorite solution (10%, 14.00 mmol) was added slowly, followed by saturated sodium thiosulphate solution (50 ml). The two layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried (MgSO4) and concentrated in vacuo to give the titled compound (3.00 g). 1H-NMR (CDCl3): 1.25-1.35 (3H), 1.55-1.64 (4H), 4.21-4.30 (2H), 10.39-10.41 (1H)

The synthetic route of 3697-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billen, Denis; Boyle, Jessica; Critcher, Douglas James; Gethin, David Morris; Hall, Kim Thomas; Kyne, Graham Michael; US2006/287365; (2006); A1;,
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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. 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate

Preparation of intermediate 5B:l-(((5-bromopyrimidin-2-yl)oxy)methyl)cyclopropane carboxylic acid ethyl ester5-Bromo-2-hydroxypyrimidine (850 mg, 4.86 mmol) and triphenylphosphine (1.91 g, 7.3 mmol) were dissolved in THF, to which was added diisopropyl azodicarboxylate DIAL) (1.19 mL, 6 mmol). The reaction solution was stirred at room temperature for 1 h, after which was added l-(hydroxymethyl)cyclopropanecarboxylic acid ethyl ester 5A (700 mg, 4.86 mmol). The reaction proceeded overnight at room temperature under stirring. The solvents were evaporated and the residue was purified with a silica gel column (n-hexane: ethyl acetate = 20: 1) to give 580 mg of white solid 5B. Yield: 39.7%.MS (ESI, m/z): [M+H]+: 300.9; 1H-NMR (300 MHz, CDC13): 8.55 (s, 2H), 4.53 (s, 2H), 4.16 (q, 2H, J= 7.2 Hz), 1.41(dd, 2H, J = 4.2 Hz, J = 3.0 Hz), 1.23 (t, 3H, J= 7.2 Hz), 1.06 (dd, 2H, J = 4.2 Hz, J= 3.0 Hz).

According to the analysis of related databases, 3697-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIJING HANMI PHARMACEUTICAL CO., LTD; ZHANG, Bo; YANG, Jun; LIU, Jinming; HUANG, Hai; WU, Yong; TAO, Ran; XU, Jiangcheng; SHEN, Ning; MOON, Sunghwan; KIM, Maengsup; WO2013/56679; (2013); A1;,
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3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C7H12O3

REFERENCE EXAMPLE 1 Preparation of 2-bromomethylcyclopropanecarboxylic acid ethyl ester (2-formyl)cyclopropanecarboxylic acid ethyl ester (14.2 g, 0.10 mol) was dissolved in methanol (200 ml). The solution was cooled to 0 C., and sodium borohydride (3.8 g, 0.10 mol) was added. The mixture was stirred for 20 minutes. After distilling off the solvent, a saturated sodium chloride aqueous solution was added thereto. The product was extracted with chloroform, then dried and concentrated. Then, it was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (2-hydroxymethyl)cyclopropanecarboxylic acid ethyl ester (14.3 g, yield: 99%). The (2-hydroxymethyl)cyclopropanecarboxylic acid ethyl ester (14.3 g, 0.1 mol) was dissolved in N,N-dimethylformamide (150 ml), and triphenylphosphine (25.9 g, 0.1 mol) was added thereto at room temperature. The mixture was stirred for 10 minutes. After cooling the mixture to 20 C., bromine (15.8 g, 0.1 mol) was dropwise added thereto over a period of 10 minutes. One hour later, the reaction mixture was added to a saturated sodium hydrogen carbonate solution, and the product was extracted with ethyl ether. It was dried, concentrated and then purified by column chromatography (hexane:ethyl acetate=5:1) to obtain (2-bromomethyl)cyclopropane carboxylic acid ethyl ester (15.3 g, yield: 74%). 1 NMR(CDCl3) delta0.9-1.0(m, 1H), 1.27(t, J=7.6 Hz, 3H), 1.3-1.5(m, 1H), 1.6-1.7(m, 1H, 1.8-2.0(m, 1H), 3.3-3.4(m, 2H), 4.25(q, J=7.6 Hz, 2H)

The synthetic route of 3697-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Glass Company, Ltd.; US5416231; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3697-68-5, The chemical industry reduces the impact on the environment during synthesis 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, I believe this compound will play a more active role in future production and life.

To a solution of ethyl l-(hydroxymethyl)cyclopropane-l-carboxylate (3.0 g, 21 mmol) in DCM (50 mL) at -10 C was added DAST (6.0 g, 40 mmol) under Ar. The reaction mixture was stirred as it warmed to ambient temperature over 1 h and continued to stir at that temperature for 23 h. An aqueous solution of HC1 (10%, 5 drops) and H20 (50 mL) were added, and the layers were separated. The aqueous layer was extracted with DCM (50 mL) and the combined organic phases were washed sequentially with H20 (50 mL) and brine (50 mL), dried (MgS04), and filtered. The filtrate was concentrated in vacuo to give ethyl l-(fluoromethyl)cyclopropane-l- carboxylate (3.0 g, yield:99%), which was carried forward without further purification.

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, Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; SCHULZ, Juergen; NEVALAINEN, Marta; DECHANTSREITER, Michael; (273 pag.)WO2019/222101; (2019); A1;,
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Some common heterocyclic compound, 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, molecular formula is C7H12O3, 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. Formula: C7H12O3

[0373] To a stirring ice-cooling solution of compound 72(200 mg, 1.39 mmol) and triethylamine (280 mg, 2.77 mmol)in DCM (10 ml), was added methanesulfonyl chloride (190mg, 1.66 mmol, dissolve in 1 ml DCM) dropwise. The reactionmixture was stirred 1 hat oo C., then diluted with DCM(20 ml), the organic phase was washed with water and brine,dried over Na2S04 , filtered and concentrated to afford crudecompound 73 (300 mg, yield 97%) as a colorless oil, useddirectly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3697-68-5, its application will become more common.

Reference:
Patent; Gao, Daxin; Yang, Heping; Yu, Yajun; US2014/329800; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, molecular formula is C7H12O3, 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. Application In Synthesis of Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate

In a three-necked flask fitted with thermometer, dropping funnel and gas exhaust, 7.39 g (58.19 mmol) of oxalyl chloride were initially charged in 116 ml of abs. dichloromethane at -78 C. 9.08 g (116.38 mmol) of dimethyl sulphoxide, dissolved in 8 ml of abs. dichloromethane, were then slowly added dropwise (careful: intensive evolution of gas), with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 5 min 7.63 g (52.90 mmol) of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (described in M. H. Parker et al. U.S. Pat. Appl. Publ., 20120053146), dissolved in 196 ml of abs. dichloromethane, were then slowly added dropwise, with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 10 min 26.72 g (264.51 mmol) of triethylamine were then slowly added dropwise, with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 10 min and then warmed to RT over 2 h. The mixture was diluted with 700 ml of methyl tert-butyl ether, the precipitate was filtered off and the filtrate was concentrated at 30 C. and 100 mbar. The residue was purified by flash chromatography (mobile phase: dichloromethane). This gave 7.30 g (97% of theory, purity about 95% according to NMR) of the title compound. (0307) 1H NMR (500 MHz, CDCl3): delta [ppm]=1.32 (t, 3H), 1.58-1.63 (m, 2H), 1.65-1.70 (m, 2H), 4.28 (q, 2H), 10.41 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3697-68-5, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; GROMOV, Alexey; FOLLMANN, Markus; BROCKSCHNIEDER, Damian; STASCH, Johannes-Peter; MARQUARDT, Tobias; TERSTEEGEN, Adrian; WUNDER, Frank; REDLICH, Gorden; LANG, Dieter; LI, Volkhart Min-Jian; (46 pag.)US2016/145271; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, 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. Recommanded Product: 3697-68-5

A 100-mL round-bottom flask was charged with ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate (1.91 g, 13.3 mmol, 1.00 equiv), TEA (4.03 g, 39.9 mmol, 3.00 equiv), and DCM (40 mL). Methanesulfonyl chloride (2.27 g, 20.0 mmol, 1.50 equiv) was added at 0 C., and the reaction mixture was stirred for 1 h at rt prior to quenching with saturated NH4Cl (30 mL). The resulting solution was extracted with dichloromethane (2*50 mL), and the organic layers were combined, washed with saturated NaHCO3 (30 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide 2.83 g (crude) of ethyl 1-(((methylsulfonyl)oxy)methyl)cyclopropane-1-carboxylate.

The synthetic route of Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; (108 pag.)US2018/134674; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 3697-68-5, Formula: C7H12O3

To a solution of ethyl 1 -(hydroxymethyl)cyclopropanecarboxylate (2.0 g, 13.87 mmol) in DCM (25 mL) was added trichloroisocyanuric acid (3.26 g, 14.01 mmol) and followed by TEMPO (0.217 g, 1.387 mmol) at-S C. The reactionmixture was stirred for 1 h at -S C. The mixture was filtered through celite, and diluted with DCM (SO mL). The solution was washed with saturated Na2CO3 (SO mL), iN HC1 (SO mL), brine (SO mL), and saturated NH4C1 (3xSO mL). The organic layer was dried over Na2504, filtered, and concentrated under reduced pressure to obtain ethyl 1-formylcyclopropanecarboxylate (1.5 g, 10.55 mmol, 76 % yield) ascolorless liquid; product was used for next step without purification. ?H NMR (CDC13, oe = 7.26 ppm, 300 MHz): oe 10.40 (s, 1 H), 4.28 (q, J= 7.1 Hz, 2 H), 1.72 – 1.56 (m, 4 H), 1.32 (t, J= 7.1 Hz, 3 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3697-68-5, 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. 3697-68-5 name is Ethyl 1-(hydroxymethyl)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.

To a solution of ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate (5.0 g, 34.7 mmol) in dichloromethane (40 mL) and triethylamine (10.5 g, 104 mmol) was added methanesulfonyl chloride (3.66 mL, 47 mmol). The mixture was stirred at 0 C. for 2 h and diluted with dichloromethane (50 mL). The solution was then washed with citric acid (2*40 mL), brine (15 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 20% ethyl acetate in petroleum ether) to give ethyl 1-(methylsulfonyloxymethyl)cyclopropanecarboxylate (3.0 g, 39%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 4.34-4.30 (m, 2H), 4.20-4.13 (m, 2H), 3.08 (s, 3H), 1.45-1.41 (m, 2H), 1.29-1.24 (m, 3H), 1.07-1.03 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; Stivala, Craig; Chen, Huifen; Daniels, Blake; US2019/127382; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C7H12O3

To a solution of Preparation 232 1-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (3.00 g, 21.00 mmol) in dichloromethane (50 ml), at 0 C., was added saturated sodium hydrogen carbonate solution (50 ml), followed by TEMPO (659 mg, 4.00 mmol) and sodium bromide (400 mg, 4.00 mmol). After stirring for 5 min, sodium hypochlorite solution (10%, 14.00 mmol) was added slowly, followed by saturated sodium thiosulphate solution (50 ml). The two layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried (MgSO4) and concentrated in vacuo to give the titled compound (3.00 g). 1H-NMR (CDCl3): 1.25-1.35 (3H), 1.55-1.64 (4H), 4.21-4.30 (2H), 10.39-10.41 (1H)

The synthetic route of 3697-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billen, Denis; Boyle, Jessica; Critcher, Douglas James; Gethin, David Morris; Hall, Kim Thomas; Kyne, Graham Michael; US2006/287365; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics