Ammonium formate → (7R,8aS)-octahydropyrrolo[1,2-a]piperazin-7-ol

HRID 861363Notes

Reaction equation

HRID 861363 reaction equation
[OH:1][C@H:2]1[CH2:17][N:5]2[CH2:6][CH2:7][N:8](CC3C=CC=CC=3)[CH2:9][C@@H:4]2[CH2:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:1][C@H:2]1[CH2:17][N:5]2[CH2:6][CH2:7][NH:8][CH2:9][C@@H:4]2[CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 14914621(7R,8aS)-2-benzyloctahydropyrrolo[1,2-a]pyrazin-7-ol

Product 1

HCID 53338751(7R,8aS)-octahydropyrrolo[1,2-a]piperazin-7-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 9.75 g (42.0 mmol) of (7R,8aS)-7-hydroxy-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Diafi, L.; et al. J. Het. Chem., 1990, 27, 2181) and 29.4 mL of 5M ammonium formate in 140 mL of methanol was treated with an aqueous slurry of 4.9 g of 10% palladium on carbon and the mixture was stirred at ambient temperature for 18 h. The mixture was filtered through Celite and evaporated to give (7R,8aS)-7-hydroxy-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine as a clear oil.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-27f407edef0948c88a4d4f5cd5303eb8
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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