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

HRID 1457967Notes

Reaction equation

HRID 1457967 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 155126511-Benzhydrylazetidin-3-yl 4-methylbenzenesulfonate

Procedure

1-Benzhydryl-3-hydroxyazetidine is allowed to react with p-toluenesulfonyl chloride using an acid-removing agent to give 1-benzhydryl-3-(p-toluenesulfonyloxy)azetidine. This compound is allowed to react with diethyl malonate in the presence of a base to give diethyl (1-benzhydryl-3-azetidinyl)malonate.

Sources & evidence

ORD record
ord-32638a1608284f35961f31aecd80df47
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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