m-Chloroperbenzoic acid → 3-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine-1-oxide

HRID 575960Notes

Reaction equation

HRID 575960 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:16][CH3:17])[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].ClC1C=C(C=CC=1)C(OO)=[O:23]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:16][CH3:17])[CH2:13][CH2:12][N+:11]([O-:23])([CH2:14][CH3:15])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 462192223-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine

Product 1

HCID 462193523-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine-1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Example 32: Enantiomer 1 of 3-(3,4-difluorophenyl)-1-ethyl-3-methoxypyrrolidine (0.009 g, 0.037 mmol), dichloromethane (2 ml), 3-chloroperoxybenzoic acid (77%) (0.017 g, 0.075 mmol). The crude product was analyzed by LCMS (Qtrap, Applied Biosystems, Q1 MS), analysis showed <95% conversion: MS (m+1)/z; 258 (M+1, bp), 257 (7), 226 (3), 214 (5), 211 (3).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-a2d1e27773394aafbe9f37ca5c0c5d2e
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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