7-N-(tert-Butoxycarbonyl)-8-[(benzyloxy)methyl]-2-(trifluoromethyl)-5,6,7,8 tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine → 7-N-(tert-Butoxycarbonyl)-8-(hydroxymethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

HRID 133077Notes

Reaction equation

HRID 133077 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=[C:10]2[CH:9]1[CH2:21][O:22]CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:19])([F:18])[F:20])[N:16]=[C:10]2[CH:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 693624067-N-(tert-Butoxycarbonyl)-8-[(benzyloxy)methyl]-2-(trifluoromethyl)-5,6,7,8 tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazineHCID 178418361HCID 178418361, compound

Product 1

HCID 693626567-N-(tert-Butoxycarbonyl)-8-(hydroxymethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 733 mg (1.8 mmol) of 7-N-(tert-butoxycarbonyl)-8-[(benzyloxy)methyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine in 8.0 mL of ethanol was added 400 mg of 10% palladium on carbon. The mixture was stirred under an atmosphere of hydrogen for 29 h. TLC analysis indicated that starting material was present. Thus 400 mg of 10% palladium on carbon was added and the mixture shaken on a Parr apparatus under 42 psi hydrogen for 12 h. The reaction mixture was filtered through Celite and concentrated. Flash chromatography (silica gel, 7% to 50% ethyl acetate/hexane gradient) gave the title compound as a white solid. LC/MS 267 (M+1-tBu).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c1da6db279b849428d6ea6c3c1ca41e3
Source dataset
uspto-grants-2008_06
Patent number
US07390809B2

Reaction notes

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