Diisopropylethylamine → Rac-n-[(3s,4r)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-4-methoxy-n-methyl-3-trifluoromethyl-benzamide

HRID 1951062Notes

Reaction equation

HRID 1951062 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].[CH2:16]([N:23]1[CH2:27][C@@H:26]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[C@H:25]([NH:36][CH3:37])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH2:16]([N:23]1[CH2:27][C@@H:26]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[C@H:25]([N:36]([CH3:37])[C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:5]=2)[CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27752984-Methoxy-3-(trifluoromethyl)benzoyl chlorideHCID 67233850(3S,4R)-1-benzyl-4-(3,4-dichlorophenyl)-N-methylpyrrolidin-3-amine

Product 1

HCID 67025727Rac-n-[(3s,4r)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-4-methoxy-n-methyl-3-trifluoromethyl-benzamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-methoxy-3-trifluoromethyl-benzoyl chloride (commercially available) (0.88 g, 2.76 mmol) in CH2Cl2 (10 ml) was added drop wise to a stirred solution of rac-[(3S,4R)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-amine (0.80 g, 2.38 mmol) and ethyl-diisopropyl-amine (0.61 ml, 3.58 mmol) in CH2Cl2 (10 ml). The reaction mixture was stirred 4 h, concentrated under vacuo and purification by flash chromatography (SiO2, CH2Cl2/MeOH, 99:1) yielded 1.09 g (86%) of the title product as colorless oil. ES-MS m/e: 537.5 (M+H+).

Workup

  1. concentrationconcentrated under vacuo and purification by flash chromatography (SiO2, CH2Cl2/MeOH, 99:1)

Sources & evidence

ORD record
ord-c9715bc0686b486ea160f8878ef33a9d
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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