Potassium Cyanide → 6-{(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-[(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidin-1-yl}-6-oxo-hexanenitrile

HRID 910468Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([N:8]1[CH2:12][CH:11]([N:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([F:26])[CH:17]=2)[CH3:14])[CH:10]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:9]1)=[O:7].[C-:35]#[N:36].[K+]>CN(C=O)C>[Cl:34][C:29]1[CH:28]=[C:27]([CH:10]2[CH:11]([N:13]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([F:26])[CH:17]=3)[CH3:14])[CH2:12][N:8]([C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][C:35]#[N:36])[CH2:9]2)[CH:32]=[CH:31][C:30]=1[Cl:33]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of 5-bromo-1-{(3SR,4RS)-3-(3,4-dichloro-phenyl)-4-[(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidin-1-yl}-pentan-1-one (XV-1) (40 mg, 0.068 mmol) in DMF (2 ml) was added potassium cyanide (5.0 mg, 0.077 mmol) and 18 crown 6-ether (18 mg, 0.068 mmol). The reaction mixture was stirred at 40° C. overnight, concentrated under vacuo. The product was purified by preparation HPLC to yield 3.2 mg (9%) of the title product as a colorless oil. ES-MS m/e: 530.1 (M+H+).

Workup

concentrationconcentrated under vacuo
customThe product was purified by preparation HPLC

Sources & evidence

ORD record: ord-4d9d5688753f4c208e8841fbc7ec357c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022099B2

Reaction notes

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