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

HRID 1087619
Notes
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Reaction equation

HRID 1087619 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 15629267(3S,5R)-5-Hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

Product 1

HCID 15629275(2S, 4R)-1-(4-Toluenesulfonyl)-2-(chloromethyl)-4-(4-toluenesulfonyloxy)-pyrrolidineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperatureAfter 6 hours the mixture was cooled with an ice bath
  2. customA white precipitate formed which
  3. customwas isolated via filtration
  4. temperatureheated
  5. temperatureto reflux for 30 minutes
  6. temperatureThe mixture was then cooled
  7. filtrationthe solids were filtered
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes