Nitromethane → tert-Butyl 3-hydroxy-3-(nitromethyl)azetidine-1-carboxylate

反応式

[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:13]([CH3:16])([O-:15])=[O:14].C(N(CC)CC)C>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([OH:12])([CH2:16][N+:13]([O-:15])=[O:14])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

実験手順

3-Oxoazetidine-1-carboxylic acid tert-butyl ester (500 mg, 2.9 mmol) was dissolved in ethanol (1.5 mL) and to this was added nitromethane (0.6 mL) and triethylamine (cat.). The reaction was stirred for eighteen hours and the solvent was then removed under reduced pressure to yield the title compound as a white solid (650 mg, 97%). δH (d6-DMSO) 6.42 (1H, s), 4.86 (2H, s), 4.04 (2H, d, J 9.2 Hz), 3.75 (2H, d, J 9.2 Hz), 1.39 (9H, s). LCMS (ES+) RT (pH 10) 1.73 min (M−H)− 231.