Potassium Carbonate → HCID 68519636, compound

HRID 899136Notes

Reaction equation

HRID 899136 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[C:11]([O:15][C:16]([N:18]1[CH2:25][CH:24]2[O:26][CH:20]([CH2:21][NH:22][CH2:23]2)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]2[O:26][CH:24]([CH2:23][N:22]([CH2:7][C:6]3[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[CH2:21]2)[CH2:25]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 68519636HCID 68519636, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-Cyanobenzyl bromide (2 g, 0.01 mol), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (2.33 g, 0.01 mol; see WO 01/28992) and potassium carbonate (3.52 g, 0.026 mol) were taken in dry acetonitrile (25 mL) and stirred at 60° C. overnight under a nitrogen atmosphere. The reaction mixture was cooled to rt, filtered and the filtrate concentrated under reduced pressure. The residue obtained thereby was purified by column chromatography (using 5% ethyl acetate in petroleum ether) to yield 2.6 g of the sub-title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue obtained
  5. customthereby was purified by column chromatography (using 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-a6763e0eb8b64b5eb24e30438f92be4e
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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