2-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acetic acid → tert-Butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate

Participants

Reaction Steps

A solution of 2-(1-(tert-butoxycarbonyl)azetidin-3-yl)acetic acid (529 mg, 2.46 mmol) in THF (5.29 mL) was cooled to 0° C. and treated with a borane-methyl sulfide complex 2M in THF (2.46 mL, 4.92 mmol), then slowly warmed to rt. After stirring for 18 h, the reaction mixture was quenched by drop-wise addition of 2 N NaOH (7 mL) then extracted with dichloromethane (4×30 mL). The organic layers were combined, dried (MgSO4), and concentrated to give tert-butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate (495 mg, 2.46 mmol, 100%) as a colorless oil. 1H NMR (CDCl3) δ: 3.96 (t, J=8.3 Hz, 2H), 3.47-3.64 (m, 4H), 2.50-2.67 (m, 1H), 1.73-1.86 (m, 2H), 1.37 (s, 9H).

Provenance & Evidence