2-Chloro-3-ethyl-4-fluorobenzonitrile → 2-Chloro-3-ethyl-4-[[(1S)-2-hydroxy-2-methyl-cyclopentyl]amino]benzonitrile

HRID 245070Notes

Reaction equation

HRID 245070 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C:4]1([CH3:9])[OH:8].[Cl:10][C:11]1[C:18]([CH2:19][CH3:20])=[C:17](F)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]>>[Cl:10][C:11]1[C:18]([CH2:19][CH3:20])=[C:17]([NH:2][C@H:3]2[CH2:7][CH2:6][CH2:5][C:4]2([OH:8])[CH3:9])[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 579086952-Chloro-3-ethyl-4-fluorobenzonitrileHCID 86693769(2S)-2-amino-1-methyl-cyclopentanol hydrochloride

Product 1

HCID 866937802-Chloro-3-ethyl-4-[[(1S)-2-hydroxy-2-methyl-cyclopentyl]amino]benzonitrile

Procedure

2-Chloro-3-ethyl-4-[[(1S)-2-hydroxy-2-methyl-cyclopentyl]amino]benzonitrile is prepared essentially as described in Example 1 using (2S)-2-amino-1-methyl-cyclopentanol hydrochloride (Preparation 18) and 2-chloro-3-ethyl-4-fluoro-benzonitrile. The crude material (350 mg) is purified using silica gel chromatography (20-60% EtOAc/hexane) to obtain Diastereomer 1 (cis) (82 mg) and Diastereomer 2 (trans) (29 mg).

Workup

  1. customThe crude material (350 mg) is purified
  2. customto obtain Diastereomer 1 (cis) (82 mg) and Diastereomer 2 (trans) (29 mg)

Sources & evidence

ORD record
ord-b91f345106b04b868e0f65ce672534ab
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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