m-Chloroperbenzoic acid → 3-(3,4-Difluorophenyl)-3-methoxy-1-methylpyrrolidine-1-oxide

HRID 1188174Notes

Reaction equation

HRID 1188174 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:15][CH3:16])[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].ClC1C=C(C=CC=1)C(OO)=[O:22]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:15][CH3:16])[CH2:13][CH2:12][N+:11]([O-:22])([CH3:14])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 462192283-(3,4-Difluorophenyl)-3-methoxy-1-methylpyrrolidine

Product 1

HCID 462193543-(3,4-Difluorophenyl)-3-methoxy-1-methylpyrrolidine-1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Example 32: Enantiomer 1 of 3-(3,4-difluorophenyl)-3-methoxy-1-methylpyrrolidine (0.009 g, 0.039 mmol), dichloromethane (2 ml), 3-chloroperoxybenzoic acid (77%) (0.018 g, 0.08 mmol). The crude product was analyzed by LCMS (Qtrap, Applied Biosystems, Q1 MS), analysis showed <95% conversion: MS (m+1)/z; 244 (M+1, bp), 243 (8), 214 (4), 197 (4), 142 (4).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-c057e0a12343451c9e9b6ccc132e1218
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

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