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

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°.

1. temperatureThe reaction solution is cooled to 3° in an ice bath
2. stirringstirred for 1 hour
3. customThe suspension obtained
4. customis evaporated under reduced pressure
5. customthe water is removed azeotropically twice with 10 ml of toluene
6. stirringthe residue is stirred up three times
7. additionwith 10 ml of a 95:5 mixture of methylene chloride and methanol
8. filtrationThe insoluble residue is filtered off
9. customthe filtrate is evaporated under reduced pressure
10. customThe crude product obtained (1.14 g)
11. filtrationfiltered off

ORD record

ord-033838e05eeb4ea3887e3377a10894f1

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05688946