Diisopropylethylamine → n-[(3s,4r)-1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-2-(3-chloro-phenyl)-n-methyl-isobutyramide

HRID 1365913Notes

Reaction equation

HRID 1365913 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:13])([CH3:12])[C:9](Cl)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:14]([N:21]1[CH2:25][C@@H:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C@H:23]([NH:33][CH3:34])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH2:14]([N:21]1[CH2:25][C@@H:24]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[C@H:23]([N:33]([CH3:34])[C:9](=[O:10])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)([CH3:13])[CH3:12])[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 139875312-(3-Chlorophenyl)-2-methylpropanoyl chlorideHCID 66940475rel-(3S,4R)-1-Benzyl-4-(4-fluorophenyl)-N-methylpyrrolidin-3-amine

Product 1

HCID 66940796n-[(3s,4r)-1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-2-(3-chloro-phenyl)-n-methyl-isobutyramideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(3-chloro-phenyl)-2-methyl-propionyl chloride (the preparation of which is described in DE2659404) (0.10 g, 0.46 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) (0.11 g, 0.38 mmol) and ethyl-diisopropyl-amine (0.10 ml, 0.58 mmol) in CH2Cl2 (5 ml). The reaction mixture was stirred 2 h, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/H, 1:3) yielded 0.14 g (80%) of the title product as light yellow oil. ES-MS m/e: 465.2 (M+H+).

Workup

  1. customthe preparation of which
  2. concentrationconcentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/H, 1:3)

Sources & evidence

ORD record
ord-a371c76c66e042d080626834f97e49ed
Source dataset
uspto-grants-2011_02
Patent number
US07893062B2

Reaction notes

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