[(2-Isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-ylcarbamoyl)methyl]carbamic acid benzyl ester → 2-amino-N-(2-isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-yl)acetamide

HRID 130381Notes

Reaction equation

HRID 130381 reaction equation
C(OC(=O)[NH:10][CH2:11][C:12](=[O:28])[NH:13][CH:14]1[CH2:24][CH:17]2[CH2:18][N:19]([CH:21]([CH3:23])[CH3:22])[CH2:20][CH:16]2[CH:15]1[CH2:25][O:26][CH3:27])C1C=CC=CC=1>Br.C(O)(=O)C.CCOCC>[NH2:10][CH2:11][C:12]([NH:13][CH:14]1[CH2:24][CH:17]2[CH2:18][N:19]([CH:21]([CH3:22])[CH3:23])[CH2:20][CH:16]2[CH:15]1[CH2:25][O:26][CH3:27])=[O:28]

Participants

5

Reactant 1

HCID 69224275[(2-Isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-ylcarbamoyl)methyl]carbamic acid benzyl ester

Product 1

HCID 692215432-amino-N-(2-isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-yl)acetamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of [(2-isopropyl-4-methoxymethyloctahydrocyclopenta[c]pyrrol-5-ylcarbamoyl)methyl]carbamic acid benzyl ester in 30% hydrogen bromide in acetic acid is stirred at room temperature until the reaction is complete. The mixture is diluted with ether and the precipitated material is purified by trituration with additional ether, followed if necessary by reverse phase HPLC and lyophilization, providing the title product.

Workup

  1. customthe precipitated material is purified by trituration with additional ether

Sources & evidence

ORD record
ord-77fb7989be7445cc91d6d34c24064b7e
Source dataset
uspto-grants-2008_06
Patent number
US07381738B2

Reaction notes

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