(3aR,5R,6aR)-Methyl 2-benzyl-5-((tert-butoxycarbonyl)amino)octahydro-cyclopenta[c]pyrrole-3a-carboxylate → rac-methyl (3aR,5R,6aR)-5-(((tert-butoxy)carbonyl)amino)-octahydrocyclopenta(c)pyrrole-3a-carboxylate

HRID 571351Notes

Reaction equation

HRID 571351 reaction equation
C([N:8]1[CH2:12][C@@:11]2([C:24]([O:26][CH3:27])=[O:25])[CH2:13][C@H:14]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][C@H:10]2[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[C:20]([O:19][C:17]([NH:16][C@@H:14]1[CH2:15][C@H:10]2[CH2:9][NH:8][CH2:12][C@@:11]2([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 86708893(3aR,5R,6aR)-Methyl 2-benzyl-5-((tert-butoxycarbonyl)amino)octahydro-cyclopenta[c]pyrrole-3a-carboxylate

Product 1

HCID 86708894rac-methyl (3aR,5R,6aR)-5-(((tert-butoxy)carbonyl)amino)-octahydrocyclopenta(c)pyrrole-3a-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product from Step C (28.6 g, 76.4 mmol) in methanol (200 mL) was added 5% palladium hydroxide on carbon (0.26 g). Hydrogenation proceeded overnight in Parr shaker at rt at 50 psi. Filtration and evaporation to dryness gave the product as a yellow gel. 1H-NMR (400 MHz, CDCl3): δ 1.44 (s, 9H), 1.72-1.90 (m, 2H), 1.93-2.05 (m, 1H), 2.05-2.17 (m, 1H), 2.67 (dd, J=11.6, 5.8 Hz, 1H), 2.77 (d, J=12.1 Hz, 1H), 2.82-2.94 (m, 1H), 3.30 (dd, J=11.6, 8.1 Hz, 1H), 3.44-3.57 (m, 2H), 3.68-3.79 (m, 3H), 4.14 (d, J=6.3 Hz, 1H), 4.85 (d, J=5.8 Hz, 1H). LC/MS: C14H24N2O4: m/z 285.2 (M+H).

Workup

  1. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-6d16943d921549e19488f2e896fb8913
Source dataset
uspto-grants-2015_05
Patent number
US09024017B2

Reaction notes

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