Potassium Carbonate → HCID 68487786, compound

HRID 16497Notes

Reaction equation

HRID 16497 reaction equation
Cl.[CH:2]12[NH:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][C:4](=[O:10])[CH2:3]2.Br[CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:10]=[C:4]1[CH2:3][CH:2]2[N:9]([CH2:12][C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[CH:6]([CH2:7][CH2:8]2)[CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 130912188-Azabicyclo[3.2.1]octan-3-one hydrochloride

Product 1

HCID 68487786HCID 68487786, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A slurry of 8-azabicyclo[3.2.1]octan-3-one hydrochloride salt (0.52 g, 3.2 mmol) and methyl 4-(bromomethyl)benzoate (0.75 g, 3.3 mmol) in 30 mL of acetonitrile was stirred as solid potassium carbonate (1.9 g, 13.6 mmol) was added. After 4 days, the reaction was filtered. The filtrate was concentrated. Purification by chromatography on silica gel using hexane gave 0.66 g of methyl 4-[(3-oxo-8-azabicyclo[3.2.1]oct-8-yl)methyl]-benzoate.

Workup

  1. additionwas added
  2. filtrationthe reaction was filtered
  3. concentrationThe filtrate was concentrated
  4. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-b3403bfde8a94ec1be5c180ae01a6829
Source dataset
uspto-grants-2010_06
Patent number
US07737145B2

Reaction notes

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