Benzene → HCID 11253896, compound

Participants

Reaction Conditions

Reaction Steps

A 2.0 M solution of (trimethylsilyl)diazomethane in diethyl ether (5.0 mL, 10.0 mmol) was added over 10 min to a solution of (1S,2R)-2-tert-butoxycarbonylamino-1-cyclohexanecarboxylic acid (0.994 g, 4.09 mmol; purchased from NeoMPS) in a 1:1 mixture of benzene and methanol (50 mL) at 25° C. The resulting mixture was stirred at 25° C. for 30 min, and then was partitioned between half-saturated sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL). The combined organic layers were dried over sodium sulfate, decanted, and were concentrated in vacuo to afford the desired product, (1S,2R)-2-tert-butoxycarbonylamino-1-cyclohexanecarboxylic acid methyl ester (1.00 g, 3.89 mmol, 95%), as a colorless oil. 1H NMR (400 MHz, CDCl3) δ: 1.44 (9H, s), 1.58-1.68 (3H, m), 1.72-1.81 (2H, m), 1.98-2.05 (2H, m), 2.77-2.80 (1H, m), 3.69 (3H, s), 3.82-3.90 (1H, m), 5.29-5.31 (1H, m). LC-MS (ESI) calcd for C13H23NO4 257.16, found 258.2 [M+H+].

Provenance & Evidence