Methanol → HCID 178484021, compound

Participants

Reaction Steps

0.898 g (3.0 mmol) of trans-3-{4-[(tert-butoxycarbonyl-methyl-amino)-methyl]-cyclohexyl}-propionic acid dissolved in 10.0 ml of tetrahydrofuran were added slowly and at 0° C. to 4.5 ml of an 1M solution of boran-tetrahydrofuran-complex in tetrahydrofuran. The reaction mixture was then stirred at room temperature for 1 hour. Subsequently, 10 ml of methanol were added and the reaction mixture evaporated. It was then poured into 50 ml of an ice/water/aqueous sodium hydrogen carbonate mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 4:1 v/v mixture of dichloromethane and ether as the eluent giving 0.690 g (80.6%) trans-[4-(3-hydroxy-propyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS: 286 (MH+).

Provenance & Evidence