Ethyl 6-acetyl-8-(benzyloxy)-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate → Ethyl 6-acetyl-2-(4-fluorobenzyl)-8-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

HRID 494086Notes

Reaction equation

HRID 494086 reaction equation
[C:1]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:12](=[O:13])[C:7]2=[C:6]([O:22]CC2C=CC=CC=2)[C:5]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:3])[CH3:2]>[OH-].[OH-].[Pd+2].C(O)C>[C:1]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[C:12](=[O:13])[C:7]2=[C:6]([OH:22])[C:5]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 68865319Ethyl 6-acetyl-8-(benzyloxy)-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

Product 1

HCID 68865212Ethyl 6-acetyl-2-(4-fluorobenzyl)-8-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-acetyl-8-(benzyloxy)-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate (140 mg, 0.30 mmol) and Pearlman's catalyst (5.0 mg, 20% Pd(OH)2 on carbon) in ethanol (20 mL) was stirred under an atmosphere of hydrogen gas (1 atm) at room temperature overnight. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under vacuum to provide the titled product.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4fe79d817c88407e8111e9c1221fb95f
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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