Tetrahydrofuran → HCID 18940470, compound

Participants

Reaction Conditions

Reaction Steps

A tetrahydrofuran solution (10 ml) of 1.2 g of t-butyl 2-benzyloxycarbonylamino-3-hydroxy-3-[5-(1-pyrrolidinyl)methyl-2-thienyl]propionate (A form) was added dropwise to 500 mg of lithium aluminum hydride in tetrahydrofuran:ether (1:1) mixed solution (50 ml) in an ice bath, and the resulting mixture was stirred for 2 hours under reflux at 50° C. Excess lithium aluminum hydride was decomposed with ether:methanol (4:1) mixed solution, and the resulting solution was mixed with 1N sodium hydroxide aqueous solution (2.5 ml) and the mixture was stirred overnight. After removing the insoluble materials by filtration, the resulting filtrate was evaporated under reduced pressure, and the thus obtained residue was subjected to silica gel column chromatography and elution was carried out with chloroform:methanol (20:1) and (10:1) and chloroform:methanol:concentrated aqueous ammonia (200:20:1) and (100:10:1) in that order to obtain 410 mg of 2-methylamino-1-[5-(1-pyrrolidinyl)methyl-2-thienyl]propane-1,3-diol (A form).

Provenance & Evidence