4-Toluenesulfonyl chloride → (2S,4R)-benzyl 4-(tosyloxy)-2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

HRID 1087629Notes

Reaction equation

HRID 1087629 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][C@H:6]([OH:8])[CH2:5][N:4]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:9]([N:4]1[CH2:5][C@H:6]([O:8][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:7][C@H:3]1[CH2:2][O:1][S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)(=[O:27])=[O:26])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chloride2×HCID 44118840HCID 44118840, compound

Product 1

HCID 14994792(2S,4R)-benzyl 4-(tosyloxy)-2-((tosyloxy)methyl)pyrrolidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cold solution of 150 g (596.9 mmol) of (2R,4S)-2-hydroxymethyl-4-hydroxy-N-(carbobenzyloxy)pyrrolidine in 0.5 1 of pyridine was added 250 g (1.32 mol) of 4-toluenesulfonyl chloride in 3 portions to keep the temperature of the reaction below 15° C. for 1 hour and then warmed to room temperature. After 12 hours, an additional 125 g (656 mmol) of p-toluenesulfonyl chloride was added and the mixture was allowed to stir at room temperature for 16 additional hours. The mixture was then cooled with an ice bath and 3 1 of 10% aqueous HC1 solution was carefully added. The mixture was extracted with 2 x 250 ml of methylene chloride and dried over MgSO4. Evaporation of the solvent provided 274 g of the product as an oil (82% yield). NMR(CDC13): 7.70 & 7.40 (m,9H, aromatic), 5.0 (m,3H), 4.43 (dd,1H), 4.12 (m,1H), 4.02 (m,H), 3.70 (m,1H), 3.88 (m,1H), 2.42 (m,6H), 2.15 (m,2H).

Workup

  1. customthe temperature of the reaction below 15° C. for 1 hour
  2. temperatureThe mixture was then cooled with an ice bath
  3. addition3 1 of 10% aqueous HC1 solution was carefully added
  4. extractionThe mixture was extracted with 2 x 250 ml of methylene chloride
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-09e704b57a084ab4849a3fba60a77607
Source dataset
uspto-grants-1991_07
Patent number
US05036153

Reaction notes

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