3-(Benzyloxy)-5-bromopyridine → (3aS,6aS)-tert-butyl 1-(5-(benzyloxy)pyridin-3-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 240530

Reaction equation

HRID 240530 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:16]1[CH2:20][CH2:19][C@H:18]2[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][C@@H:17]12>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N:16]2[CH2:20][CH2:19][C@H:18]3[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][C@@H:17]23)[CH:12]=[N:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 153891983-(Benzyloxy)-5-bromopyridineHCID 16227750rac-tert-butyl (3aR,6aR)-octahydropyrrolo(3,4-b)pyrrole-5-carboxylate

Product 1

HCID 66757415(3aS,6aS)-tert-butyl 1-(5-(benzyloxy)pyridin-3-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Procedure

3-(Benzyloxy)-5-bromopyridine and (3aS,6aS)-tert-butyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (prepared as described in WO2001081347) were processed as described in Example 53B to provide the title compound. MS(ESI) m/z 396 (M+H)+.

Sources & evidence

ORD record
ord-37088ac12b674121b125fefc5ed5f897
Source dataset
uspto-grants-2014_02
Patent number
US08648084B2

Linked notes

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