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. 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C11H14ClNO2
To a solution of (3R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1 .0]hexane-3- carboxylic acid (syn-anti diastereoisomer mixture 10/2) (D27) (3.06 g, 13.5 mmol) in dry DMF (15 ml) under N2 atmosphere HOBT.H20 (2.06 g, 13.46 mmol), EDC.HCI (3.87 g, 20.20 mmol), methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (3.06 g, 13.46 mmol) and TEA (4.7 ml, 33.7 mmol) were added in sequence. The mixture was stirred for 2 hrs at RT, then the solvent was evaporated in vacuo and the residue taken up in AcOEt (500ml), washed twice with water (50 ml), dried over Na2SO4 and evaporated to afford a residue which was loaded on a SNAP-Si cartridge (100g) and eluted with a mixture DCM/AcOEt from 10/0 to 9/1 . Collected fractions after solvent evaporation afforded the two diastereoisomer (D73a) (2.55 g) and (D73b) (880 mg). (D73a) (syn diastereoisomer) MS: (ES/+) m/z: 401 .4 [MH+] C22H28N2O5 requires 400.20 1 H NMR (400 MHz, DMSO-d6) delta (ppm): 8.70 (s, 1 H), 7.90 – 7.76 (m, 2 H), 7.34 – 7.19 (m, 2 H), 4.52 – 4.35 (m, 1 H), 3.84 (s, 3 H), 3.43 – 3.32 (m, 1 H), 2.67 -2.39 (m, 1 H), 1 .88 – 1 .74 (m, 1 H), 1 .52 – 1 .33 (m, 10 H), 1 .27 – 1 .12 (m, 4 H), 1 .09 – 0.92 (m, 1 H), 0.66 – 0.53 (m, 1 H). (D73b) (anti diastereoisomer) MS: (ES/+) m/z: 401 .4 [MH+] C22H28N2O5 requires 400.20 1 H NMR (400 MHz, DMSO-d6) delta (ppm): 8.69 – 8.52 (s, 1 H), 7.90 – 7.73 (m, 2 H), 7.35 – 7.19 (m, 2 H), 3.93 – 3.75 (m, 4 H), 3.36 – 3.30 (m, 1 H), 2.35 – 2.19 (m, 1 H), 2.12 – 2.02 (m, 1 H), 1 .90 – 1 .74 (m, 1 H), 1 .47 – 1 .30 (m, 9 H), 1 .25 – 1 .07 (m, 4 H), 0.73 (td, J = 5.4, 8.8 Hz, 1 H), 0.39 (br. s., 1 H).
The synthetic route of 1014645-87-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; PUCCI, Sabrina; STASI, Luigi, Piero; ROVATI, Lucio; WO2013/4290; (2013); A1;,
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