Diethyl 1-benzylazetidine-3,3-dicarboxylate → [1-Benzyl-3-(hydroxymethyl)azetidin-3-YL]methanol

반응식

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:17][C:16]([C:23](OCC)=[O:24])([C:18](OCC)=[O:19])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[NH3:14].[CH2:7]([N:14]1[CH2:17][C:16]([CH2:18][OH:19])([CH2:23][OH:24])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

실험 절차

LiAlH4 (1.0 M in THF, 65 mL, 65 mmol) was added dropwise to a solution of diethyl 1-benzylazetidine-3,3-dicarboxylate (1.0 g, 3.43 mmol) in THF (20 mL). The resulting suspension was stirred overnight at room temperature, quenched with water (0.25 mL), 15% aq. NaOH (0.25 mL), and water (0.75 mL), filtered through celite, and concentrated in vacuo. Chromatography (7N NH3 in MeOH/CH2Cl2=5:95→10:90) of the resulting residue afforded 4 (450 mg, 63%) as an oil. 1H NMR (CDCl3): δ 7.33-7.20 (m, 5H), 3.74 (s, 4H), 3.65 (s, 2H), 3.12 (s, 4H). 13C NMR (CDCl3): δ 137.4, 129.02, 128.8, 127.7, 66.8, 63.3, 58.7, 41.0. HRMS for C12H17NO2 [M+] calcd, 207.1259; found, 207.1259.