1-Aminocyclohexanecarboxylic acid → Methyl 1-aminocyclohexanoate

Participants

Reaction Steps

In a round-bottomed flask 1-amino-1-cyclohexanecarboxylic acid (1.00 g, 7.0 mmol) was suspended in dichloromethane (26 mL) and MeOH (13 mL). (Trimethylsilyl)diazomethane (2.0 M in hexanes, 6.0 mL, 12.0 mmol) was added dropwise and the reaction mixture gradually became homogeneous as it was stirred at room temperature overnight. The reaction mixture was quenched with a small portion of acetic acid and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated aqueous Na2CO3. The aqueous layer was extracted with dichloromethane and the combined organics were dried over Na2SO4 and concentrated to afford 1.15 g of 1-amino-1-cyclohexanecarboxylic acid methyl ester as a light yellow oil.

Provenance & Evidence