Synthetic Route of 1014645-87-4,Some common heterocyclic compound, 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, molecular formula is C11H14ClNO2, 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.
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.H2O (2.06 g, 13.46 mmol), EDC.HCl (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 (500 ml), washed twice with water (50 ml), dried over Na2SO4 and evaporated to afford a residue which was loaded on a SNAP-Si cartridge (100 g) 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 400.201H NMR (400 MHz, DMSO-d6) delta (ppm): 8.70 (s, 1H), 7.90-7.76 (m, 2H), 7.34-7.19 (m, 2H), 4.52-4.35 (m, 1H), 3.84 (s, 3H), 3.43-3.32 (m, 1H), 2.67-2.39 (m, 1H), 1.88-1.74 (m, 1H), 1.52-1.33 (m, 10H), 1.27-1.12 (m, 4H), 1.09-0.92 (m, 1H), 0.66-0.53 (m, 1H).(D73b) (anti diastereoisomer)MS: (ES/+) m/z: 401.4 [MH+] C22H28N2O5 requires 400.201H NMR (400 MHz, DMSO-d6) delta (ppm): 8.69-8.52 (s, 1H), 7.90-7.73 (m, 2H), 7.35-7.19 (m, 2H), 3.93-3.75 (m, 4H), 3.36-3.30 (m, 1H), 2.35-2.19 (m, 1H), 2.12-2.02 (m, 1H), 1.90-1.74 (m, 1H), 1.47-1.30 (m, 9H), 1.25-1.07 (m, 4H), 0.73 (td, J=5.4, 8.8 Hz, 1H), 0.39 (br. s., 1H).
The synthetic route of 1014645-87-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Borriello, Manuela; Pucci, Sabrina; Stasi, Luigi Piero; Rovati, Lucio; US2015/87626; (2015); A1;,
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