Cyanogen Bromide → HCID 45100915, compound

Participants

Reaction Steps

To a stirred mixture of (2S,4S)-2-amino-4-(3-benzyloxy-phenoxy)-hexan-1-ol (90 mg) and sodium acetate (46 mg) in methanol (2 ml) under an argon atmosphere was added a solution of cyanogen bromide (37 mg) in methanol (1 ml). The mixture was stirred for 18 hours then diluted with 1 N aqueous sodium hydroxide solution. The mixture was extracted twice with dichloromethane and the combined organic phases were dried over sodium sulphate and concentrated in vacuo. The crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; gradient: dichloromethane/MeOH 100:0→95:5) to afford (S)-4-[(S)-2-(3-benzyloxy-phenoxy)-butyl]-4,5-dihydro-oxazol-2-ylamine (69 mg, 71%) as a light yellow gum. MS (ISP): 341.1 ([M+H]+).

Provenance & Evidence