Aluminium lithium hydride → 5-Oxo-4-(3-oxo-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester
反応式
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][C:18](=[O:23])N(OC)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH:18]=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]参加物
3
実験手順
To a cooled (−78° C.) solution of 4-[2-(methoxy-methyl-carbamoyl)-ethyl]-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester 3 g (9 mmol) was added dropwise a solution of lithium aluminum hydride 9.1 ml (9 mmol, 1 M solution in THF). The mixture was quenched by addition of acetone and then AcOH. The reaction was allowed to reach RT after which time water and 10% aq. KHSO4 solution were added and the mixture repeatedly extracted with TBME. The combined organic was washed with brine, dried (MgSO4) and concentrated. Purification by flash column chromatography (EtOAc:MeOH 19:1) afforded the title compound 1.5 g (61%) as a colorless oil. MS: 271.5 (MH+).