Di-tert-butyl dicarbonate → HCID 67130060, compound

HRID 1038811Notes

Reaction equation

HRID 1038811 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:15][CH:16]=[C:10]2[CH2:9]1)C1C=CC=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>[OH-].[OH-].[Pd+2].CO>[CH:16]1[N:15]=[C:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[N:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=12

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 67130059HCID 67130059, compound

Product 1

HCID 67130060HCID 67130060, compoundYield 109%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a flask was added tert-butyl (7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-3-yl)methylcarbamate (0.500 g, 1.46 mmol, prepared using O from Preparation #S.1 with Boc2O), MeOH (20 mL) and Pd(OH)2 on carbon (20 wt %, 0.255 g, 0.363 mmol). The mixture was evacuated and purged with N2 three times and a H2 balloon was fitted to the flask. The flask was purged with H2 three times and stirred for about 6 h at rt. The mixture was filtered and the solvent was removed under reduced pressure to give tert-butyl (5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-3-yl)methylcarbamate (0.40 g, 109%): LC/MS (Table 2, Method e) Rt=1.58 min; MS m/z: 253 (M+H)+.

Workup

  1. customprepared
  2. customThe mixture was evacuated
  3. custompurged with N2 three times
  4. customa H2 balloon was fitted to the flask
  5. customThe flask was purged with H2 three times
  6. filtrationThe mixture was filtered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f948a1a6fd2437ba698da44d7fbce89
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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