HCID 14514526, compound → (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 703517Notes

Reaction equation

HRID 703517 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([O:15]CC2C=CC=CC=2)=[O:14])[CH2:11][C@@H:10]2[CH2:23][CH2:24][CH2:25][C@H:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][C@@H:10]2[CH2:23][CH2:24][CH2:25][C@H:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 14514526HCID 14514526, compound

Product 1

HCID 15622962(2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

56.5 g (0.163 mol) of benzyl N-tert.-butoxycarbonyl-(2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate are hydrogenated in 400 ml of ethanol with 2 g of palladium on charcoal as catalyst at 20° C. and under 1.1 bar. 40.4 g of the title compound are obtained. Rf (SiO2, EtOAc/MeOH=20:1) 0.45.

Sources & evidence

ORD record
ord-cf135f1b9dd343959b48a00c318d3826
Source dataset
uspto-grants-1991_01
Patent number
US04983623

Reaction notes

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