Acetonitrile → HCID 69883189, compound

HRID 431000Notes

Reaction equation

HRID 431000 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[O:10][C@H:11]([CH2:14]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2].[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[C:36]1([OH:44])[CH2:42][CH:41]2[NH:43][CH:38]([CH2:39][CH2:40]2)[CH2:37]1.C([O-])([O-])=O.[K+].[K+].C(#N)C>C(Cl)(Cl)Cl.CO.O>[CH2:1]([O:3][C:4]1[C:9]2[O:10][CH:11]([CH2:14][N:43]3[CH:38]4[CH2:39][CH2:40][C@H:41]3[CH2:42][C:36]([C:27]3[CH:28]=[CH:29][C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:26]=3)([OH:44])[CH2:37]4)[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 11184346HCID 11184346, compoundHCID 12095852HCID 12095852, compound

Product 1

HCID 69883189HCID 69883189, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584188Chloroform methanolSolvent

Procedure

To 117 mg (0.32 mmol) (S)-toluene-4-sulfonic acid 8-ethoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester was added 84 mg (0.33 mmol) 3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octan-3-ol, 95.0 mg K2CO3, and 7 mL acetonitrile. The reaction was refluxed and was monitored by TLC on a silica gel plate using CHCl3:MeOH (10:1) as eluent. After 18 h, the mixture was transferred to a separatory funnel containing 50 mL water. The aqueous layer was extracted with CH2Cl2 (2×25 mL), washed with brine, dried over Na2SO4, filtered and evaporated to an oil. The crude material was purified by flash chromatography on silica gel, using a gradient elution of CHCl3:MeOH (40:1 to 20:1). The appropriate fractions were combined and evaporated to afford 68.1 mg (0.15 mmol, a 48% yield) of the title compound as a tan solid.

Workup

  1. temperatureThe reaction was refluxed
  2. customthe mixture was transferred to a separatory funnel
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×25 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to an oil
  8. customThe crude material was purified by flash chromatography on silica gel
  9. washa gradient elution of CHCl3:MeOH (40:1 to 20:1)
  10. customevaporated
  11. customto afford 68.1 mg (0.15 mmol

Sources & evidence

ORD record
ord-28f0a67aa30d47869ff8e77c955777a0
Source dataset
uspto-grants-2003_12
Patent number
US06656951B2

Reaction notes

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