Iodosylbenzene → N-[(1S)-1-(4-{3-[3,5-bis(trifluoromethyl)-phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}phenyl)ethyl]cyclopropane-carboxamide

HRID 2206898Notes

Reaction equation

HRID 2206898 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]2([C:32]([F:35])([F:34])[F:33])[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([C@@H:24]([NH:26][C:27]([CH:29]4[CH2:31][CH2:30]4)=[O:28])[CH3:25])=[CH:20][CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.I(C1C=CC=CC=1)=[O:39]>ClCCl>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C:13]2([C:32]([F:35])([F:34])[F:33])[CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[CH:20][C:21]([C@@H:24]([NH:26][C:27]([CH:29]4[CH2:31][CH2:30]4)=[O:28])[CH3:25])=[CH:22][CH:23]=3)[CH:14]2[OH:39])[CH:4]=[C:3]([C:2]([F:36])([F:1])[F:37])[CH:8]=1

Participants

4

Reactant 2

HCID 92125IodosylbenzeneHCID 53261930N-[(1S)-1-(4-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl)phenyl)-ethyl]cyclopropanecarboxamide

Product 1

HCID 87160555N-[(1S)-1-(4-{3-[3,5-bis(trifluoromethyl)-phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}phenyl)ethyl]cyclopropane-carboxamideYield 11.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(1S)-1-(4-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl)phenyl)-ethyl]cyclopropanecarboxamide (cf. Japanese Patent Application No. 2009-296889) (200 mg) was dissolved in dichloromethane (10 mL), and to the reaction solution was added Fe(salen) (12 mg) and iodosobenzene (98 mg). The resulting mixture was stirred at room temperature for 20 hours. Under reduced pressure, the solvent was distilled off and the residues were purified by silica gel column chromatography to obtain N-[(1S)-1-(4-{3-[3,5-bis(trifluoromethyl)-phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}phenyl)ethyl]cyclopropane-carboxamide (24 mg).

Workup

  1. distillationUnder reduced pressure, the solvent was distilled off
  2. customthe residues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a6c52183f2c14a6ca0818ee16cc7f4a3
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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