HCID 68953666, compound → HCID 68951105, compound

HRID 238983Notes

Reaction equation

HRID 238983 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[NH:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)[CH2:9]1

Participants

4

Reactant 1

HCID 68953666HCID 68953666, compound

Product 1

HCID 68951105HCID 68951105, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-[3-((S)-1-benzyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethyl-benzene sulfonamid (620 mg, 1.34 mmol) (Example 65) in methanol (30 ml) was hydrogenated using the ThalesNano H-Cube® hydrogenation reactor employing a 10% palladium on charcoal catalyst cartridge. After concentration of the solution under reduced pressure, the crude product was purified with silica gel chromatography with ethyl acetate/methanol (1:1; 0:1) as eluent, yielding 328 mg of the purified product.

Workup

  1. customAfter concentration of the solution under reduced pressure, the crude product was purified with silica gel chromatography with ethyl acetate/methanol (1:1; 0:1) as eluent

Sources & evidence

ORD record
ord-4d2c758317574cf5b280cd3ca1a9495d
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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