Thionyl Chloride → (2R,5R)-1-((4-(Chloromethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)methyl)-2,5-dimethylpyrrolidine

HRID 1662476Notes

Reaction equation

HRID 1662476 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C@@H:6]1[CH2:10][CH2:9][C@@H:8]([CH3:11])[N:7]1[CH2:12][C:13]1[CH:18]=[C:17]([CH2:19]O)[CH:16]=[CH:15][C:14]=1[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[F:29]>C(Cl)Cl>[Cl:3][CH2:19][C:17]1[CH:16]=[CH:15][C:14]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=2[F:29])=[C:13]([CH2:12][N:7]2[C@H:8]([CH3:11])[CH2:9][CH2:10][C@H:6]2[CH3:5])[CH:18]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57706802(2-(((2R,5R)-2,5-Dimethyl-1-pyrrolidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

Product 1

HCID 57705528(2R,5R)-1-((4-(Chloromethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)methyl)-2,5-dimethylpyrrolidineYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.25 g, 2.1 mmol) was added to a solution of 66.71B (0.029 g, 0.084 mmol) in DCM (0.7 mL) and the mixture was stirred at room temperature for 1 hour. After removing solvent, 66.71C (28 mg) was obtained.

Workup

  1. customAfter removing solvent

Sources & evidence

ORD record
ord-8f59a5ea0b594214868b9f7be59ad421
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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