Trifluoroacetic acid → Rac-[(3r,4s)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

HRID 1951075Notes

Reaction equation

HRID 1951075 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]([N:24]2[CH2:29][CH2:28][N:27]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:26][CH2:25]2)=[O:23])[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]([N:24]3[CH2:25][CH2:26][N:27]([S:30]([CH3:33])(=[O:31])=[O:32])[CH2:28][CH2:29]3)=[O:23])[CH2:12]2)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67026227rac-[(3S,4R)-4-(3,4-Dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 58009203Rac-[(3r,4s)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanoneYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-[(3S,4R)-4-(3,4-dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (130 mg, 0.24 mmol) in CH2Cl2 (5 ml) was added TFA (1 ml) at RT. Stirring was continued over night. 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 100 mg (92%) of the title compound as light yellow oil. ES-MS m/e: 435.37 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-4edebc7a64cc4032b863302cb835fdd5
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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