Benzene → rac-methyl (1R,2S)-2-aminocycloheptane-1-carboxylate hydrochloride

Participants

Reaction Conditions

Reaction Steps

cis-2-Amino-cycloheptanecarboxylic acid hydrochloride (0.75 g, 3.89 mmol) was dissolved in methanol (5 mL). Benzene (7.5 mL) was added followed by the dropwise addition of a 2.0 M solution of (trimethylsilyl)diazomethane in dichloromethane (3.5 mL). The yellow solution continued to stir at 25° C. for 20 min. The solution was concentrated in vacuo to afford a yellow powder. The powder was suspended in methanol (20 mL) and concentrated in vacuo to afford the desired product, cis-2-amino-cycloheptanecarboxylic acid methyl ester hydrochloride (0.8 g, 3.86 mmol, 99%), as a white powder. 1H NMR (400 MHz, D2O) δ: 1.33-1.86 (8H, m), 2.60-2.62 (1H, m), 2.75-2.78 (1H, m), 3.27-3.30 (1H, m), 3.39-3.44 (1H, m), 3.62 (3H, s).

Provenance & Evidence