benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-ylcarbamate → (3-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol

HRID 473099Notes

Reaction equation

HRID 473099 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([NH:16]C(=O)OCC1C=CC=CC=1)[CH2:11][CH2:10]2>[Pd].C(O)C>[NH2:16][CH:12]1[C:13]2[C:9](=[CH:8][C:7]([CH2:6][C:5]3[CH:4]=[C:3]([CH2:2][OH:1])[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=3)=[CH:15][CH:14]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 70223911benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-ylcarbamate

Product 1

HCID 66734486(3-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanolYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-ylcarbamate (1.04 g, 2.28 mmol) and 10% palladium on carbon (38 mg) in ethanol (20 mL) was placed under hydrogen (balloon) and stirred at rt for 1 h. The mixture was filtered over Celite and concentrated under reduced pressure. The white solid was triturated with diethyl ether to afford the title compound as a white solid (660 mg, 90%). MS (ESI): m/z [M+NH2]+ 305.2

Workup

  1. filtrationThe mixture was filtered over Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe white solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-2a99d4b30d72445ca6bfc1befc03c4bd
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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