L-Tartaric acid → (3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-ol

HRID 2216366Notes

Reaction equation

HRID 2216366 reaction equation
[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].C(O)(=O)[C@@H]([C@H](C(O)=O)O)O>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 444305L-Tartaric acidHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

Product 1

HCID 946095(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-olYield 13.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.1 g of 3-ethynyl-3-quinuclidinol and 15 g of L-(+)-tartaric acid were dissolved under heating in 300 ml of methanol. After standing to cool, the resulting crystals were collected by filtration and recrystallized from methanol for three times, to give 2.07 g of the title compound.

Workup

  1. temperatureto cool
  2. filtrationthe resulting crystals were collected by filtration
  3. customrecrystallized from methanol for three times

Sources & evidence

ORD record
ord-045b0c00c94e4f619c268e6d07eafcb6
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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