Bicarbonate Ion → Tert-butyl 3-(1-hydroxy-2-methylpropyl)azetidine-1-carboxylate

Participants

Reaction Steps

Sodium borohydride (237 mg, 6.26 mmol) was added to a solution of 3-(isobutyryl)azetidine-1-carboxylic acid tert-butyl ester (0.95 g, 4.18 mmol) in ethanol (7.5 mL). The resulting reaction mixture was stirred at RT for 2 h. Saturated hydrogen carbonate (25 mL) was added and the resulting mixture was stirred for further 15 min. The aqueous phase was extracted with dichloromethane (3×25 mL). The organic layer was dried over sodium sulfate and the solvents reduced in vacuo to give the crude product as yellow oil. The residue was purified by column chromatography (Si—PCC, ethyl acetate:cyclohexane: gradient 0:100 to 40:60). The solvents were reduced in vacuo to afford the title compound as colourless oil (840 mg, 88%). 1H NMR (400 MHz, CDCl3): δ 3.91-3.90 (3 H, m), 3.71 (1 H, dd, J=8.54, 6.04 Hz), 3.51 (1 H, dd, J=7.21, 4.97 Hz), 2.70-2.63 (1 H, m), 1.65-1.63 (1 H, m), 1.44 (9 H, s), 0.90 (6 H, t, J=6.59 Hz).

Provenance & Evidence