Aluminium lithium hydride → 5-Oxo-4-(3-oxo-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

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Reaction Steps

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+).

Provenance & Evidence