Ethyl Acetate → 1,1-Dimethylethyl 3-hydroxy-3-(2-hydroxy-1,1-dimethylethyl)-1-azetidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 3-(2-(ethoxycarbonyl)propan-2-yl)-3-hydroxyazetidine-1-carboxylate (0.50 g, 1.74 mmol) in DCM (5 ml) was cooled to −78° C. A solution of DIBAL-H in DCM (5.23 mmol, 5.23 ml, 1M) was added dropwise and the solution allowed to warm to 0° C. and stirred for 4 hrs. Sat NH4Cl (20 ml) and ethyl acetate (40 ml) was added. The organic layer washed with brine (30 ml), dried (Na2SO4), and concentrated to give an oil. The oil was purified by flash column chromatography eluting with 30 to 70% ethylacetate/hexanes to give the title compound as a colorless oil 0.20 g, 47%. 1H NMR (CDCl3, 400 Mhz) 1.01 (6H, s), 1.43 (9H, s), 3.58 (2H, s), 3.75 (2H, d), 4.03 (2H, d).

Provenance & Evidence