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

HRID 1594589Notes

Reaction equation

HRID 1594589 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 hours. 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-535fa0f255134dd197f25f4803cfb644
Source dataset
uspto-grants-2001_09
Patent number
US06284757B1

Reaction notes

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