benzyl (3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate → (3aS,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-ol

HRID 1959431Notes

Reaction equation

HRID 1959431 reaction equation
[OH:1][CH:2]1[C@@H:6]2[CH2:7][N:8](C(OCC3C=CC=CC=3)=O)[CH2:9][C@@H:5]2[CH2:4][CH2:3]1>C1COCC1.CO.[Pd]>[CH2:9]1[C@@H:5]2[CH2:4][CH2:3][CH:2]([OH:1])[C@@H:6]2[CH2:7][NH:8]1

Participants

5

Reactant 1

HCID 66744449benzyl (3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate

Product 1

HCID 55299595(3aS,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyl (3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (850 mg, 3.3 mmol) and Pd/C (200 mg) in THF (5.000 mL) was hydrogenated at 25-30 psi in a Parr shaker. After 12 h, the reaction mixture was diluted with MeOH and filtered through a plug of celite. The solvents were removed under reduced pressure to obtain (3aS,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-ol in quantitative yield.

Workup

  1. filtrationfiltered through a plug of celite
  2. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-795f9d192c0a4db984680222b2d88aac
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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