2-Benzyl-hexahydro-cyclopenta[c]pyrrole-3a-carboxylic acid methyl ester → Methyl octahydrocyclopenta[c]pyrrole-3a-carboxylate

HRID 712225Notes

Reaction equation

HRID 712225 reaction equation
C([N:8]1[CH2:12][C:11]2([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:14][CH2:15][CH:10]2[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[CH2:9]1[CH:10]2[CH2:15][CH2:14][CH2:13][C:11]2([C:16]([O:18][CH3:19])=[O:17])[CH2:12][NH:8]1

Participants

4

Reactant 1

HCID 41183282-Benzyl-hexahydro-cyclopenta[c]pyrrole-3a-carboxylic acid methyl ester

Product 1

HCID 66977181Methyl octahydrocyclopenta[c]pyrrole-3a-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-benzyloctahydrocyclopenta[c]pyrrole-3a-carboxylate (2.0 g, 7.69 mmol) in MeOH (15.0 mL) was added palladium hydroxide (0.20 g, 10% w/w) and the mixture stirred at rt for 16 h under H2 atmosphere. After completion of reaction (by TLC), the reaction mixture was passed through celite and the solvent evaporated. The crude (1.50 g) residue was carried forward for the next step without further purification. MS: 170.18 [M+H]+.

Workup

  1. customAfter completion of reaction (by TLC)
  2. customthe solvent evaporated
  3. customThe crude (1.50 g) residue was carried forward for the next step without further purification

Sources & evidence

ORD record
ord-09a6abba829b491280d5efffeeb37fb7
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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