Potassium Hydroxide → 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

HRID 861425Notes

Reaction equation

HRID 861425 reaction equation
[C:1]([C:3]1([O:11]C(=O)CCC)[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1)#[CH:2].[OH-].[K+]>CO>[C:1]([C:3]1([OH:11])[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1)#[CH:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54501015HCID 54501015, compound

Product 1

HCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above oil containing (-)-3-ethynyl-3-butyryloxyquinuclidine was treated with a solution of potassium hydroxide (2.24 g) in methanol (50 ml). The mixture was stirred at ambient temperature for 2 hours. The mixture was evaporated and deionised water (2 ml) was added to the residue to give a solid. The solid was collected by filtration, washed with water (2×2 ml) and dried under vacuum over phosporus pentoxide to give (-)-3-ethynyl-3-hydroxyquinuclidine (611 mg) as a solid, m.p. 199°-202° C., [α]19D =-56.1° (C=1.02, methanol).

Workup

  1. customThe mixture was evaporated
  2. additiondeionised water (2 ml) was added to the residue
  3. customto give a solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with water (2×2 ml)
  6. customdried under vacuum over phosporus pentoxide

Sources & evidence

ORD record
ord-d3b718e015a84ebb8bb8afd963eeeedd
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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