Sodium hydride → HCID 58348398, compound

HRID 2192357Notes

Reaction equation

HRID 2192357 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([OH:9])[CH2:2]2.C[O:11][C:12]([C:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=O.[H-].[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([O:9][C:12]([C:14]1([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)=[O:11])[CH2:2]2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 7364113-Quinuclidinol, (+)-HCID 59179615Methyl 1-phenylcycloheptanecarboxylate

Product 1

HCID 58348398HCID 58348398, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-(+)-3-quinuclidinol (299 mg) and 1-phenyl-cycloheptanecarboxylic acid methyl ester (Example 14d) (455 mg) in 6.5 mL dry toluene under nitrogen was treated with a 60% dispersion of sodium hydride (94 mg) and the mixture was heated to reflux for 24 h then cooled to room temperature and allowed to stand over the weekend. EtOAc and sat. NaHCO3 (aq) were added and the phases separated. The aqueous phase was extracted with EtOAc (×3) and the combined organic layer was washed with brine, dried (MgSO4) and evaporated to afford the crude product. Purification was achieved by silica gel chromatography eluting with 0-10% MeOH/dichloromethane to give the sub-titled compound (384 mg) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 h
  3. customthe phases separated
  4. extractionThe aqueous phase was extracted with EtOAc (×3)
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto afford the crude product
  9. customPurification
  10. washeluting with 0-10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-3be63ae4b32d47829acf0611986a8008
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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