Hydrochloric Acid → (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol

Participants

Reaction Steps

1.42 g (3.86 mmol) of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-cyclopropylhydroxymethyl]-2,2-dimethyl-3-oxazolidinecarboxylate dissolved in 15 ml of methanol and 10 ml of water are treated with 4 ml of 7.5N hydrochloric acid and stirred at 50° for 3 hours. The reaction solution is cooled to 3° in an ice bath, treated dropwise with 4 ml of 7.5N sodium hydroxide solution and stirred for 1 hour. The suspension obtained is evaporated under reduced pressure, the water is removed azeotropically twice with 10 ml of toluene and the residue is stirred up three times with 10 ml of a 95:5 mixture of methylene chloride and methanol. The insoluble residue is filtered off and the filtrate is evaporated under reduced pressure. The crude product obtained (1.14 g) is suspended in 15 ml of ether and thereafter filtered off. There is obtained 0.58 g of (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol as colourless crystals, m.p. 141°-142°.

Provenance & Evidence