4-Toluenesulfonyl chloride → Benzyl (3R)-3-[(4-methylbenzene-1-sulfonyl)oxy]pyrrolidine-1-carboxylate

HRID 1109729Notes

Reaction equation

HRID 1109729 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([O:19][C:20]([N:22]1[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[CH2:12]([O:19][C:20]([N:22]1[CH2:26][CH2:25][C@@H:24]([O:27][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol

Product 1

HCID 15197576Benzyl (3R)-3-[(4-methylbenzene-1-sulfonyl)oxy]pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

22.25 g (0.117 moles) of toluene-4-sulfonyl chloride, dissolved in 30 ml of pyridine, were added dropwise to a stirred solution of 11.79 g (0.053 moles) of (3R)-N-benzyloxycarbonyl-3-hydroxypyrrolidine [J. Chem. Soc., Chem. Commun. 1984, 1298]in 50 ml of pyridine, cooled below 0° C. After the addition, the reaction mixture was kept at 5° C. for 48 hours.

Workup

  1. additionAfter the addition

Sources & evidence

ORD record
ord-04d8c6ae40974c97b2c7e8b3c112179f
Source dataset
uspto-grants-1994_06
Patent number
US05322848

Reaction notes

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