4-Bromo-3,5-dimethylphenol → (R)-3-(4-Bromo-3,5-dimethyl-phenoxy)-1-methanesulfonyl-pyrrolidine

HRID 471454Notes

Reaction equation

HRID 471454 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH3:11][S:12]([N:15]1[CH2:19][CH2:18][C@H:17](OS(C)(=O)=O)[CH2:16]1)(=[O:14])=[O:13]>>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][C@@H:17]2[CH2:18][CH2:19][N:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH2:16]2)=[CH:4][C:3]=1[CH3:10]

Participants

3

Reactant 2

HCID 819704-Bromo-3,5-dimethylphenolHCID 59816083(3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate

Product 1

HCID 86703888(R)-3-(4-Bromo-3,5-dimethyl-phenoxy)-1-methanesulfonyl-pyrrolidine

Procedure

The title compound is prepared in analogy to Intermediate 36 from 4-Bromo-3,5-dimethylphenol (626 mg, 3.08 mmol) and Methanesulfonic acid (S)-1-methanesulfonyl-pyrrolidin-3-yl ester (300 mg, 1.23 mmol). (Yield: 350 mg).

Sources & evidence

ORD record
ord-483e8023e88646b98d3928fe1c10eef0
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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