Potassium Carbonate → tert-Butyl 2-{7-[4-(4-pyridinyl)butyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}ethylcarbamate

HRID 500511Notes

Reaction equation

HRID 500511 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:18][CH:17]3[O:19][CH:13]([CH2:14][NH:15][CH2:16]3)[CH2:12]2)=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C([O-])([O-])=O.[K+].[K+]>CC#N>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:18][CH:17]3[O:19][CH:13]([CH2:14][N:15]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:16]3)[CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 18540442HCID 18540442, compound

Product 1

HCID 9909198tert-Butyl 2-{7-[4-(4-pyridinyl)butyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}ethylcarbamateYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

3-[4-(4-Pyridinyl)butyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane (0.25 g, 0.96 mmol, from step (ii) above), tert-butyl 2-bromoethylcarbamate (0.26 g, 0.98 mmol, see Preparation R above) and K2CO3 (0.4 g, 2.9 mmol) were mixed in CH3CN (10 mL) and stirred at 50° C. overnight. The reaction mixture was filtered, evaporated and purified by chromatography on silica (DCM:6% MeOH (satd. with NH3)). Additional purification by extraction with ether:KHSO4, basification of the organic phase and extraction with DCM gave the title compound in 51% yield.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. custompurified by chromatography on silica (DCM:6% MeOH (satd. with NH3))
  4. customAdditional purification
  5. extractionby extraction with ether
  6. extractionKHSO4, basification of the organic phase and extraction with DCM

Sources & evidence

ORD record
ord-31e927015e5f41fda853be5783485499
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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