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

HRID 575958Notes

Reaction equation

HRID 575958 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

To a stirred solution of enantiomer 2 of 3-(3,4-difluorophenyl)-1-ethyl-3-methoxypyrrolidine (0.011 g, 0.045 mmol) in dichloromethane (2 ml) was added 3-chloroperoxybenzoic acid (77%) (0.0204 g, 0.09 mmol). The mixture was stirred at room temperature for 30 min and was then filtrated through a plug of aluminiumoxid (basic) which was eluted with dichloromethane:MeOH (9:1). The crude product was analyzed by LCMS (Qtrap, Applied Biosystems, Q1 MS). analysis showed <95% conversion: MS (m+1)/z; 258 (M+1, bp), 259 (23), 257 (3), 214 (7), 142 (5).

Workup

  1. filtrationwas then filtrated through a plug of aluminiumoxid (basic) which
  2. washwas eluted with dichloromethane:MeOH (9:1)

Sources & evidence

ORD record
ord-bbce59563010447aaa4ef7d60bd8b00a
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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