rel-1,1-Dimethylethyl (4aR,7aR)-octahydro-1H-pyrrolo(3,4-b)pyridine-1-carboxylate → tert-butyl cis-6-(6-chloro-3-pyridinyl)octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

HRID 393782Notes

Reaction equation

HRID 393782 reaction equation
[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5][CH2:4][C@@H:3]2[CH2:7][NH:8][CH2:9][C@H:2]12.Br[C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[N:22][CH:23]=1>>[Cl:24][C:21]1[N:22]=[CH:23][C:18]([N:8]2[CH2:7][C@@H:3]3[C@@H:2]([N:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5][CH2:4]3)[CH2:9]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 1519436rel-1,1-Dimethylethyl (4aR,7aR)-octahydro-1H-pyrrolo(3,4-b)pyridine-1-carboxylateHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 86584375tert-butyl cis-6-(6-chloro-3-pyridinyl)octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylateYield 49%

Procedure

tert-Butyl cis-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (374 mg, 1.65 mmol), prepared as described in (EP0603887 A2) and 5-bromo-2-chloropyridine (314 mg, 1.65 mmol), prepared as described in (Tetrahedron Lett. (1998), 39, 2059-2062) were processed as described in Example 1E to provide the title compound (273 mg, 49% yield). MS (DCI/NH3) m/z 338/340 (M+H)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-ef520f431e084dd88869f4846db691ef
Source dataset
uspto-grants-2004_10
Patent number
US06809105B2

Reaction notes

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