Trifluoroacetic acid → [(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone

HRID 910459Notes

Reaction equation

HRID 910459 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH: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]([CH:24]2[CH2:29][CH2:28][N:27]([C:30]([C:32]3([CH3:35])[CH2:34][CH2:33]3)=[O:31])[CH2:26][CH2:25]2)=[O:23])[CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:21][C:16]1[CH:15]=[C:14]([CH:13]2[CH:9]([NH:7][CH3:6])[CH2:10][N:11]([C:22]([CH:24]3[CH2:29][CH2:28][N:27]([C:30]([C:32]4([CH3:35])[CH2:33][CH2:34]4)=[O:31])[CH2:26][CH2:25]3)=[O:23])[CH2:12]2)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67025619HCID 67025619, compound

Product 1

HCID 67025815[(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanoneYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {(3RS,4SR)-4-(3,4-dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester (3.02 g, 5.61 mmol) in CH2Cl2 (30 ml) was added TFA (4.3 ml). The reaction mixture was stirred at RT for 20 hours, aqueous NaHCO3 was added until pH=8 and the product was extracted with CH2Cl2. The combined organic phase were dried over Na2SO4. The product was purified by column chromatography (SiO2, H/EtOAc/MeOH, 50:50:0 to 0:90:10) to afford 1.79 g (73%) of the title product as a light brown oil. ES-MS m/e: 338.3 (M+H+).

Workup

  1. extractionthe product was extracted with CH2Cl2
  2. dry with materialThe combined organic phase were dried over Na2SO4
  3. customThe product was purified by column chromatography (SiO2, H/EtOAc/MeOH, 50:50:0 to 0:90:10)

Sources & evidence

ORD record
ord-fd67f3e762284dc7bbe56f6f9502a4de
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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