Hydrochloric Acid → (2S, 4R)-1-(4-Toluenesulfonyl)-2-(chloromethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine

HRID 1087619Notes

Reaction equation

O[CH2:2][C@H:3]1[CH2:7][C@H:6]([OH:8])[CH2:5][N:4]1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].N1C=CC=CC=1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.[ClH:36]>C(O)C>[C:15]1([CH3:18])[CH:16]=[CH:17][C:12]([S:9]([N:4]2[CH2:5][C@H:6]([O:8][S:31]([C:28]3[CH:27]=[CH:26][C:25]([CH3:35])=[CH:30][CH:29]=3)(=[O:32])=[O:33])[CH2:7][C@H:3]2[CH2:2][Cl:36])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To an ice-cold solution of 170 g (626.5 mmol) of (2R, 4S)-2-hydroxymethyl-4-hydroxy-1-(4-toluene- sulfonyl)-pyrrolidine in 0.5 1 of pyridine was added 250 g (1.32 mol) of p-toluenesulfonyl chloride in one portion and the reaction was warmed to 50° C. After 6 hours the mixture was cooled with an ice bath and 3 1 of 10% aqueous hydrogen chloride solution was carefully added. A white precipitate formed which was isolated via filtration and then taken in 1 1 of ethanol and heated to reflux for 30 minutes. The mixture was then cooled and the solids were filtered and dried under reduced pressure to give 195 g of product in 70% yield. M.P.=145°-146° C.

Workup

temperatureAfter 6 hours the mixture was cooled with an ice bath
customA white precipitate formed which
customwas isolated via filtration
temperatureheated
temperatureto reflux for 30 minutes
temperatureThe mixture was then cooled
filtrationthe solids were filtered
customdried under reduced pressure

Sources & evidence

ORD record: ord-365d4a08ffb0462899223d0d63bbe68b
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05036153

Reaction notes

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