Diisopropylethylamine → Rac-n-[(3s,4r)-1-benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-isobutyramide

HRID 1365911Notes

Reaction equation

HRID 1365911 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:21]([N:28]1[CH2:32][C@@H:31]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[C@H:30]([NH:40][CH3:41])[CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH2:21]([N:28]1[CH2:32][C@@H:31]([C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)[C@H:30]([N:40]([CH3:41])[C:14](=[O:15])[C:13]([C:5]2[CH:4]=[C:3]([C:2]([F:20])([F:19])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=2)([CH3:18])[CH3:17])[CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 66940475rel-(3S,4R)-1-Benzyl-4-(4-fluorophenyl)-N-methylpyrrolidin-3-amine

Product 1

HCID 87211944Rac-n-[(3s,4r)-1-benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-isobutyramideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride (the preparation of which is described in WO2002079134) (0.88 g, 2.76 mmol) in CH2Cl2 (5 ml) was added drop wise to a stirred solution of rac-[(3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-amine (0.72 g, 2.53 mmol) and ethyl-diisopropyl-amine (0.64 ml, 3.78 mmol) in CH2Cl2 (5 ml). The reaction mixture was stirred 1 h, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/H, 1:4) yielded 1.06 g (74%) of the title product as colorless foam. ES-MS m/e: 567.3 (M+H+).

Workup

  1. concentrationconcentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/H, 1:4)

Sources & evidence

ORD record
ord-dc3d125d7aad465ea5fa2d7f7551fd3c
Source dataset
uspto-grants-2011_02
Patent number
US07893062B2

Reaction notes

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