Benzyl 5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-ylcarbamate → (1-((1-Amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

HRID 43020Notes

Reaction equation

HRID 43020 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:29]([F:32])([F:31])[F:30])=[N:5][N:6]([CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH:14]([NH:18]C(=O)OCC2C=CC=CC=2)[CH2:13][CH2:12]3)[CH:7]=1>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:18][CH:14]1[C:15]2[C:11](=[CH:10][C:9]([CH2:8][N:6]3[CH:7]=[C:3]([CH2:2][OH:1])[C:4]([C:29]([F:32])([F:31])[F:30])=[N:5]3)=[CH:17][CH:16]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 67088172Benzyl 5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-ylcarbamate

Product 1

HCID 58230802(1-((1-Amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of palladium hydroxide (0.498 mmol, 350 mg) and benzyl 5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-ylcarbamate (2.69 mmol, 1.2 g) in ethanol (30 mL) was hydrogenated at 2 bar pressure for 30 min before the reaction vessel was vented and the whole filtered through a pad of dicalite. The pad was washed with EtOAc and the filtrate concentrated under reduced pressure. The residue was purified using SCX eluting with 2N NH3/MeOH to give a clear oil which solidified on standing (700 mg, 2.25 mmol, 83%). 1H NMR (400 MHz, CDCl3) δ 1.65 (m, 1H) 2.51 (m, 1H) 2.80 (m, 1H) 2.95 (m, 1H) 1.35 (t, 1H) 4.60 (s, 2H) 5.26 (s, 2H) 7.12 (d, 2H) 7.30 (d, 1H) 7.42 (s, 1H).

Workup

  1. filtrationthe whole filtered through a pad of dicalite
  2. washThe pad was washed with EtOAc
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified
  5. washeluting with 2N NH3/MeOH
  6. customto give a clear oil which

Sources & evidence

ORD record
ord-64dee780cfd14169a3111d140a95d687
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

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