4-Toluenesulfonyl chloride → 1-Benzylpyrrolidin-3-yl 4-methylbenzenesulfonate

HRID 1109726Notes

Reaction equation

HRID 1109726 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]([N:19]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[CH2:12]([N:19]1[CH2:23][CH2:22][CH:21]([O:24][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 69889N-benzyl-3-pyrrolidinol

Product 1

HCID 156236681-Benzylpyrrolidin-3-yl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

2.39 g (12.4 mmoles) of toluene-4-sulfonyl chloride, dissolved in 10 ml of pyridine, were added dropwise, under nitrogen atmosphere, to a stirred solution of 2.0 g (11.3 mmoles) of N- benzyl-3-hydroxypyrrolidine [J. Med. Pharm. Chem. 1, (1959) 73,76,77]in 15 ml of pyridine, cooled below -10° C.

Sources & evidence

ORD record
ord-036785c6cb2542d2a34d1350e3fcc745
Source dataset
uspto-grants-1994_06
Patent number
US05322848

Reaction notes

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