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

HRID 1951073Notes

Reaction equation

HRID 1951073 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][N:11]([C:20]([N:22]2[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]2)=[O:21])[CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:41]>>[Cl:41][C:17]1[CH:18]=[CH:19][C:14]([C@H:13]2[C@H:9]([NH:7][CH3:6])[CH2:10][N:11]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)=[O:21])[CH2:12]2)=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67026258Rac-[(3s,4r)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-4-phenyl-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 58009334Rac-[(3r,4s)-3-(4-chloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanoneYield 98%

Procedure

To a solution of rac-[(3S,4R)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-4-phenyl-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (0.86 g, 1.61 mmol) in CH2Cl2 (12 ml) was added TFA (3 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 dried over Na2SO4. Purification by flash chromatography (SiO2, CH2Cl2/MeOH 95:5) yielded 0.68 g (98%) of the title compound as a white solid. ES-MS m/e: 401.3 (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 dried over Na2SO4
  6. customPurification by flash chromatography (SiO2, CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-0ce2d4f31de44ab9b839d09e5132f805
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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