7-Methoxycarbonyl-2-phenylmethyl-1,2,3,4,8,8a-hexahydro-pyrrolo[1,2-a]pyrazin-1-one → 7-Methoxycarbonyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-1-one

HRID 861365Notes

Reaction equation

HRID 861365 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:6][CH:7]2[C:12](=[O:13])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9][N:8]2[CH:21]=1)=[O:4].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:21][N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12](=[O:13])[CH:7]2[CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 217063767-Methoxycarbonyl-2-phenylmethyl-1,2,3,4,8,8a-hexahydro-pyrrolo[1,2-a]pyrazin-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 217064047-Methoxycarbonyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-1-oneYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 40.0 g (140 mmol) of 7-methoxycarbonyl-2-phenylmethyl-1,2,3,4,8,8a-hexahydro-pyrrolo[1,2-a]pyrazin-1-one (Preparation 8) and 10 g of 5% Pd on charcoal in 600 mL of ethyl acetate was shaken in a Parr apparatus under 50 psi of hydrogen gas for 6.5 h. The mixture was filtered through Celite, and the filtrate was evaporated to give 38.4 g (95%) of the title compound. 13C NMR (CDCl3): δ 31.8, 41.4, 44.8, 46.5, 49.6, 52.1, 55.2, 64.0, 127.5, 128.1, 128.7, 128.8, 136.6, 169.6, 174.8. HRMS calcd for C16 H22N2O3 (MH+): 289.1552, found: 289.1549.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-da1fe21c1cd44c419c8a7c37be7c9789
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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