3-Chlorobenzoic Acid → 3-(2,3-Difluorophenyl)-1-propylpyrrolidin-3-OL 1-oxide

HRID 1931855Notes

Reaction equation

HRID 1931855 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:17])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH3:16])[CH2:10]1.ClC1C=C(C=CC=1)C(O)=[O:23]>ClCCl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:17])[CH2:13][CH2:12][N+:11]([O-:23])([CH2:14][CH2:15][CH3:16])[CH2:10]1

Participants

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 25143813(+)-3-(2,3-Difluorophenyl)-1-propylpyrrolidin-3-OL

Product 1

HCID 866434283-(2,3-Difluorophenyl)-1-propylpyrrolidin-3-OL 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Example 68: (−)-3-(2,3-difluorophenyl)-1-propylpyrrolidin-3-ol (1.3 g, 5.4 mmol), dichloromethane (60 ml), m-chlorobenzoic acid (2.7 g, 16.2 mmol). Yield: 1.15 g. 1H NMR (400 MHz, CHLOROFORM-d) 8 ppm 1.06 (t, J=7.41 Hz, 3H) 1.96-2.16 (m, 2H) 2.69-2.83 (m, 1H) 2.84-3.00 (m, 1H) 3.35 (dt, J=10.92, 5.46 Hz, 2H) 3.50 (br. s., 2H) 3.67 (d, J=9.75 Hz, 1H) 3.77 (d, J=10.92 Hz, 1H) 3.89-3.99 (m, 1H) 7.18 (d, J=1.56 Hz, 1H) 7.13-7.20 (m, 1H) 7.62 (td, J=6.63, 5.46 Hz, 1H)

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-0d2b819b42184ee1bfae00af898d7c33
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

Loading…