Acetyl chloride → cis-8-Benzyl-2-acetyl-2,8-diazabicyclo[4,3,0]nonane

HRID 2356383Notes

Reaction equation

HRID 2356383 reaction equation
[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][NH:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl.C(N(CC)CC)C.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][N:14]2[C:17](=[O:19])[CH3:18])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 10198297(4aS-cis-)-6-benzyl-octahydropyrrolo(3.4-b)pyridine

Product 1

HCID 67237118cis-8-Benzyl-2-acetyl-2,8-diazabicyclo[4,3,0]nonaneYield 85.5%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

The preparation comprises dissolving cis-8-benzyl-2,8-diazabicyclo[4,3,0]nonane (5.0 g, 23.1 mmol) in dichloromethane (50 mL) and triethylamine (5 mL) under stirring in ice bath, dropwise adding a solution of acetyl chloride (1.8 g, 23.1 mmol) in chloroform (10 mL), continuing with the stirring until the reaction finishes, distilling off the solvent, and chromatographing on silica gel with petroleum ether and ethyl acetate to give cis-8-benzyl-2-acetyl-2,8-diazabicyclo[4,3,0]nonane (5.1 g, 85.5%).

Workup

  1. distillationdistilling off the solvent, and chromatographing on silica gel with petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-73dba824b6a34dd4a3e3a31b28376924
Source dataset
uspto-grants-2010_07
Patent number
US07759362B2

Reaction notes

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