(+-)-3-Quinuclidinol → HCID 13371145, compound

HRID 358247Notes

Reaction equation

HRID 358247 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[Na].[CH:11]1([C:17]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([OH:23])[C:18](OCC)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[CH:11]1([C:17]([C:24]#[C:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([OH:23])[C:18]([O:9][CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 15381(+-)-3-QuinuclidinolHCID 5360545Sodium2×HCID 54432452HCID 54432452, compound

Product 1

HCID 13371145HCID 13371145, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

3-Quinuclidinol (2.5 g., 0.020 mole) was dissolved in 50 ml. of toluene and a small piece of sodium (~0.05 g.) was added. The toluene was refluxed for about 40 minutes until all the sodium had reacted. Ethyl α-cyclohexyl-α-phenylethynylglycolate (4.3 g., 0.015 mole) was subsequently added as a solution in 35 ml. of toluene, over an hour period, to the refluxing reaction mixture. The reaction mixture was refluxed for an additional 20 hours. During the last four hours about 40 ml. of solvent was distilled over. The reaction mixture was then worked-up as described previously. The basic chloroform extract yielded 4.0 g. of an oil, which partially crystallized upon the addition of anhydrous ether. A total of 1.6 g. (27%) of crude product was obtained. Recrystallization from hexane gave analytically pure material, m.p. 171°-172°.

Workup

  1. customhad reacted
  2. customto the refluxing reaction mixture
  3. temperatureThe reaction mixture was refluxed for an additional 20 hours
  4. customDuring the last four hours about 40 ml
  5. distillationof solvent was distilled over
  6. extractionThe basic chloroform extract
  7. customyielded 4.0 g
  8. customof an oil, which partially crystallized upon the addition of anhydrous ether

Sources & evidence

ORD record
ord-c04a4781f86746f4953671bf83b7c0f6
Source dataset
uspto-grants-1984_08
Patent number
US04465834

Reaction notes

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