Trifluoroacetic acid → Rac-4-[(3r,4s)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-benzonitrile

HRID 1951080Notes

Reaction equation

HRID 1951080 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:12][N:11]([C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:21][C:16]1[CH:15]=[C:14]([C@H:13]2[C@H:9]([NH:7][CH3:6])[CH2:10][N:11]([C:22]([C:23]3[CH:24]=[CH:25][C:26]([C:29]#[N:30])=[CH:27][CH:28]=3)=[O:31])[CH2:12]2)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67025575Rac-[(3s,4r)-1-(4-cyano-benzoyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 58009325Rac-4-[(3r,4s)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-benzonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-[(3S,4R)-1-(4-cyano-benzoyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (1.08 g, 2.28 mmol) in CH2Cl2 (25 ml) was added TFA (5 ml) at RT. Stirring was continued one hour. The reaction mixture was then concentrated under vacuo, the crude dissolved in CH2Cl2, washed with aq.NaHCO3 and the organic phase was dried over Na2SO4. Purification by flash chromatography (SiO2, CH2Cl2/MeOH 95:5) yielded 0.72 g (85%) of the title compound as light yellow foam. ES-MS m/e: 374.0 (M+H+).

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuo
  2. dissolutionthe crude dissolved in CH2Cl2
  3. washwashed with aq
  4. dry with materialNaHCO3 and the organic phase was dried over Na2SO4
  5. customPurification by flash chromatography (SiO2, CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-ab1b296572df459099d2d8a3b9aa6403
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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