p-(Trifluoromethoxy)benzaldehyde → 3-(4-(Trifluoromethoxy)benzyl)pyrrolidin-2-one

HRID 883136Notes

Reaction equation

HRID 883136 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.FC(F)(F)C([N:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23])=O>>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][CH:20]2[CH2:21][CH2:22][NH:18][C:19]2=[O:23])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 132941581-(Trifluoroacetyl)pyrrolidin-2-one

Product 1

HCID 684971293-(4-(Trifluoromethoxy)benzyl)pyrrolidin-2-oneYield 53%

Procedure

Following the procedure as described in Preparation 5, making variations as required to use 4-(trifluoromethoxy)benzaldehyde in place of 4-fluorobenzaldehyde to react with 1-(2,2,2-trifluoroacetyl)pyrrolidin-2-one, the title compound was obtained as a white solid in 53% yield: 1H NMR (300 MHz, CDCl3) δ 7.24-7.06 (m, 4H), 3.71-3.50 (m, 2H), 3.34-3.02 (m, 3H), 2.19-2.00 (m, 1H), 1.83-1.70 (m, 1H); MS (ES+) m/z 260.1 (M+1).

Workup

  1. customas described in Preparation 5

Sources & evidence

ORD record
ord-bea424cd25b04ee18b4ace5eeaffd5ae
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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