Ammonium Chloride → HCID 86591293, compound

HRID 720465Notes

Reaction equation

HRID 720465 reaction equation
Cl[C:2]1(Cl)[C@@H:6]2[N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9][C@@H:5]2[CH2:4][C:3]1=[O:20].[Cl-].[NH4+]>[Zn]>[O:20]=[C:3]1[CH2:2][C@@H:6]2[N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9][C@@H:5]2[CH2:4]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 86591294HCID 86591294, compound

Product 1

HCID 86591293HCID 86591293, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Azabicycles of general formula (43), (44), (45), (46) and (47), wherein R is aryl or heterocycle, R′ is alkyl and R1 is as defined in formula (I), may be prepared as described in Scheme 12. Benzyl (cis)-6,6-dichloro-5-oxohexahydrocyclopenta[b]pyrrole-1(2H)-carboxylate, prepared as described in Tetrahedron Lett. (1997) 38(11), 1869–1872, may be treated with zinc dust and ammonium chloride to provide benzyl (cis)-5-oxohexahydrocyclopenta[b]pyrrole-1(2H)-carboxylate. Benzyl (cis)-5-oxohexahydrocyclopenta[b]pyrrole-1(2H)-carboxylate may be processed as described in Schemes 2–8 to provide azabicycles of general formula (43), (44), (45), (46) and (47).

Workup

  1. custommay be prepared

Sources & evidence

ORD record
ord-b2c9fb7425ea4fd2ad29ba3b17b5ec31
Source dataset
uspto-grants-2006_11
Patent number
US07135484B2

Reaction notes

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