Trifluoroacetic acid → rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone

HRID 527472Notes

Reaction equation

HRID 527472 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:11][N:10]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([C:31]3([CH3:34])[CH2:33][CH2:32]3)=[O:30])[CH2:25][CH2:24]2)=[O:22])[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH2:7][CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:11][N:10]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([C:31]3([CH3:34])[CH2:33][CH2:32]3)=[O:30])[CH2:25][CH2:24]2)=[O:22])[CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67237329rac-(3S,4R)-{4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester

Product 1

HCID 67238593rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanoneYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-(3S,4R)-{4-(3,4-dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (5.747 g, 0.011 mol) in dichloromethane (55 mL) was added trifluoroacetic acid (8.39 mL, 0.110 mol) and the reaction mixture was stirred for 4 h at ambient temperature. The reaction mixture was basified by addition of aqueous sodium carbonate (1M, 10 mL). The organic layers were washed with water (8 mL) and the aqueous layers were extracted with dichloromethane (10 mL). The combined org. layers were dried over sodium sulfate and concentration afforded 4.30 g (92%) of the title compound as a light brown foam. ES-MS m/e: 524.2 (M+H+).

Workup

  1. washThe organic layers were washed with water (8 mL)
  2. extractionthe aqueous layers were extracted with dichloromethane (10 mL)
  3. dry with materiallayers were dried over sodium sulfate and concentration

Sources & evidence

ORD record
ord-9334293522754135a22b0df3d78012ea
Source dataset
uspto-grants-2016_05
Patent number
US09346786B2

Reaction notes

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