Methanol → 1-amino-3-propyl-5-hydroxyhexahydrocyclopenta[d]imidazole-2(1H)-one

HRID 1885899Notes

Reaction equation

HRID 1885899 reaction equation
C(=[N:8][N:9]1[CH:13]2[CH2:14][CH:15]([OH:17])[CH2:16][CH:12]2[N:11]([CH2:18][CH2:19][CH3:20])[C:10]1=[O:21])C1C=CC=CC=1.CO>[Pd].C(O)(=O)C>[NH2:8][N:9]1[CH:13]2[CH2:14][CH:15]([OH:17])[CH2:16][CH:12]2[N:11]([CH2:18][CH2:19][CH3:20])[C:10]1=[O:21]

Participants

5

Reactant 2

HCID 887MethanolHCID 679048761-Benzylideneamino-3-propyl-5-hydroxyhexahydrocylopenta[d]imidazol-2(1H)-one

Product 1

HCID 198784021-amino-3-propyl-5-hydroxyhexahydrocyclopenta[d]imidazole-2(1H)-oneYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

The compound of step (f) (7.0 g) was added to a solution of methanol (280 ml) and acetic acid (2.25 ml) containing 10% Pd on carbon (2.5 g) and the resulting mixture stirred at 15° C. under an atmosphere of hydrogen for 3 days. The catalyst was removed by filtration through Celite and concentration of the filtrate in vacuo gave the desired product as an oil (5.0 g).

Workup

  1. customThe catalyst was removed by filtration through Celite and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-a2063fc0b2c143bfb121119341426eab
Source dataset
uspto-grants-1992_09
Patent number
US05147885

Reaction notes

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