Potassium Carbonate → HCID 69843299, compound

HRID 1596481Notes

Reaction equation

HRID 1596481 reaction equation
Cl[CH2:2][C:3]([OH:16])([CH2:14][OH:15])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[CH:17]12[CH2:25][CH:21]([CH2:22][NH:23][CH2:24]1)[CH2:20][N:19]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:18]2.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:29]([O:28][C:26]([N:19]1[CH2:18][CH:17]2[CH2:25][CH:21]([CH2:22][N:23]([CH2:2][C:3]([OH:16])([CH2:14][OH:15])[CH2:4][O:5][C:6]3[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=3)[CH2:24]2)[CH2:20]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21701940HCID 21701940, compoundHCID 22490264Tert-butyl 3,7-diazabicyclo(3.3.1)nonane-3-carboxylate

Product 1

HCID 69843299HCID 69843299, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(3-chloro-2-hydroxy-2-hydroxymethylpropoxy)benzonitrile (180 mg; 0.74 mmol; from step (b) above), tert-butyl 3,7-diazabicyclo-[3.3.1]nonane-3-carboxylate (230 mg; 1.0 mmol; see Example F above) and K2CO3 (140 mg; 1.0 mmol) in MeCN (5 mL) was refluxed for 48 hours. The reaction mixture was filtered and the filtrate concentrated. The residue was dissolved in diethyl ether and the solution was acidified with KHSO4 (aq.). The aqueous layer was collected and NaHCO3 (satd.) was added followed by ether extraction. The organic layer was collected, dried, concentrated and subjected to column chromatography (DCM:MeOH; 20:1) to give the title compound in a 31% yield.

Workup

  1. temperaturewas refluxed for 48 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated
  4. dissolutionThe residue was dissolved in diethyl ether
  5. customThe aqueous layer was collected
  6. additionNaHCO3 (satd.) was added
  7. extractionfollowed by ether extraction
  8. customThe organic layer was collected
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-27b7029c167547e6bc5434b0fab4de31
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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