4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Participants

Reaction Steps

To an ice-cold, stirred solution of acid from step 1 (700 mg, 3.8 mmol) in tetrahydrofuran (10 mL) was added borane-dimethyl sulfide complex (2 mL, 4.1 mmol). The reaction mixture was warmed to room temperature for 2 h and a 1:1 mixture of acetic acid/water (10 mL) was added. The resulting mixture was concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 hexanes/ethyl acetate) provided methyl 4-(hydroxymethyl)cyclohexanecarboxylate (560 mg): 1H NMR (500 MHz, CDCl3) δ 3.68 (s, 3H), 3.51–3.46 (m, 2H), 2.59–2.57 (m, 1H), 2.05–2.00 (m, 2H), 1.65–1.55 (m, 5H), 1.31–1.27 (m, 2H).

Provenance & Evidence