Aluminium lithium hydride → HCID 86584831, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.5 g (3.5 mmol) (2S,4R)-4-(4-methoxy-benzylsulfanyl)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester dissolved in 15 ml was added to 4.2 ml (4.2 mmol, 1M THF solution) of LAH in 50 ml THF at −78° C. The reaction was was warmed up to −30° C., cooled to −78° C. and quenched with a suspension of 1.2 g silica gel/1.2 g MgSO4.7H2O in 5 ml aqueous 10% KHSO4. The suspension was stirred for 15 min at room temperature, filtered and washed with THF. After evaporation of the THF, the residue was taken up in CH2Cl2, dried over Na2SO4 and evaporated to give 1.2 g (98%) of (2S,4R)-2-formyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, MS: 351 (M+).

Provenance & Evidence