Boron trifluoride etherate → (2S, 4S)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl) pyrrolidine
Reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[C:12]1([CH3:30])[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:28][CH:27]([OH:29])[CH2:26][C@@H:22]2[C:23](O)=[O:24])(=[O:20])=[O:19])=[CH:14][CH:13]=1>C1COCC1>[OH:24][CH2:23][C@@H:22]1[CH2:26][C@H:27]([OH:29])[CH2:28][N:21]1[S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:30])=[CH:13][CH:14]=1)(=[O:20])=[O:19]Participants
Procedure
4.14 g (109.5 mmol) of sodium borohydride was suspended in 150 ml of THF at 0° C. and 17.6 ml (142.2 mmol) of borontrifluoride etherate was added dropwise over a period of 10 minutes. 15.6 g (54.7 mmol) of 1-(4-toluenesulfonyl)-4-hydroxy-D-proline was added in portions and the mixture was allowed to stir at room temperature for 16 hours. The reaction was then cooled to 0° C. and quenched with methanol: 10% aqueous HC1 solution was then added and the mixture was gently heated to 60° C. for 1 hour. The pH of the reaction was adjusted to neutral with 50% aqueous sodium hydroxide solution and the volatiles were evaporated under reduced pressure. The product was then isolated via filtration and the filter cake was washed with water. Drying under vacuum at 60° C. for 12 hours yielded 10.2 g of the product as a white solid in 69% yield. M.P.=103°-105° C.
Workup
- temperatureThe reaction was then cooled to 0° C.
- customquenched with methanol
- addition10% aqueous HC1 solution was then added
- temperaturethe mixture was gently heated to 60° C. for 1 hour
- customthe volatiles were evaporated under reduced pressure
- customThe product was then isolated via filtration
- washthe filter cake was washed with water
- customDrying under vacuum at 60° C. for 12 hours
Sources & evidence
- ORD record
- ord-779b8fe6f65b4d25863377be86fda247
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05036153
Reaction notes
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