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

HRID 473108Notes

Reaction equation

HRID 473108 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)[CH2:12][C@H:11]([NH:16]C(=O)OCC1C=CC=CC=1)[CH2:10]2.[H][H]>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:16][C@@H:11]1[CH2:10][C:9]2[C:13](=[CH:14][CH:15]=[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:8]=2)[CH2:12]1

Participants

5

Reactant 2

HCID 70222664(S)-benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 66733722(S)-(3-((2-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanolYield 86%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To (S)-benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-ylcarbamate (2.94 mmol, 1.34 g) in Ethanol (35.4 mL) was added palladium hydroxide (2.51 mmol, 0.353 g). The reaction was placed under 2 bar of hydrogen gas and allowed to stir at room temp for 30 mins. The reaction mix was filtered through a dicalite cartridge before washing with EtOH. The solvent was removed before purifying further by SCX (20 g cartridge, 1:1 MeOH/DCM wash, 2M NH3 MeOH elution). The solvent was removed to give the product as a clear gum (810 mg, 86%). MS (ESI): m/z [M+H]+ 322.2

Workup

  1. additionThe reaction mix
  2. filtrationwas filtered through a dicalite cartridge
  3. washbefore washing with EtOH
  4. customThe solvent was removed
  5. custombefore purifying further by SCX (20 g cartridge, 1:1 MeOH/DCM wash, 2M NH3 MeOH elution)
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-6802119c6a1a47c5b885c251aa403052
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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