(S)-methyl 3-((2-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate → (S)-methyl 3-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate

HRID 473114Notes

Reaction equation

HRID 473114 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:21][C:22]3[CH:23]=[C:24]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])[CH:18]=2)[CH2:13]1)=O)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:11][C@@H:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:21][C:22]3[CH:23]=[C:24]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])[CH:18]=2)[CH2:13]1

Participants

5

Reactant 2

HCID 70223635(S)-methyl 3-((2-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 70223149(S)-methyl 3-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of (S)-methyl 3-((2-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate (0.254 mmol, 123 g) and palladium hydroxide (0.064 mmol, 45 mg) in ethanol (9 mL) was treated under hydrogenation conditions (2 bar hydrogen) for 30 minutes. The reaction mixture was filtered through celite and the pad washed with EtOH & EtOAc before the filtrate was concentrated under reduced pressure to give a light brown film (82 mg, 92%). MS (ESI): m/z [M+H]+ 350.0

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe pad washed with EtOH & EtOAc before the filtrate
  3. concentrationwas concentrated under reduced pressure
  4. customto give a light brown film (82 mg, 92%)

Sources & evidence

ORD record
ord-f30052442c1a4a6bb2d7cf10d704f6b6
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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