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

HRID 1365912Notes

Reaction equation

HRID 1365912 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:14])([CH3:13])[C:10](Cl)=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:15]([N:22]1[CH2:26][C@@H:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C@H:24]([NH:34][CH3:35])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH2:15]([N:22]1[CH2:26][C@@H:25]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[C@H:24]([N:34]([CH3:35])[C:10](=[O:11])[C:9]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)([CH3:14])[CH3:13])[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 115289412-(3,5-Dichloro-phenyl)-2-methyl-propionyl chlorideHCID 66940475rel-(3S,4R)-1-Benzyl-4-(4-fluorophenyl)-N-methylpyrrolidin-3-amine

Product 1

HCID 66941003Rac-n-[(3s,4r)-1-benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-2-(3,5-dichloro-phenyl)-n-methyl-isobutyramideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(3,5-dichloro-phenyl)-2-methyl-propionyl chloride (the preparation of which is described in WO2005002577) (0.146 g, 0.58 mmol) in CH2Cl2 (4 ml) was added drop wise to a stirred solution of rac-[(3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-methyl-amine (the preparation of which is described herein above) (0.15 g, 0.52 mmol) and ethyl-diisopropyl-amine (0.13 ml, 0.79 mmol) in CH2Cl2 (5 ml). The reaction mixture was stirred 2 h, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/H, 1:4) yielded 0.18 g (68%) of the title product as light brown oil.

Workup

  1. customthe preparation of which
  2. concentrationconcentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/H, 1:4)

Sources & evidence

ORD record
ord-ba072676b1964d28b4201bf0fbb153d6
Source dataset
uspto-grants-2011_02
Patent number
US07893062B2

Reaction notes

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