Water → (3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-ol

HRID 900773Notes

Reaction equation

HRID 900773 reaction equation
C([O:4][C@@:5]1([C:13]#[CH:14])[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)(=O)C.[H-].[Na+].O>CO>[C:13]([C@:5]1([OH:4])[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)#[CH:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 9834196(3R)-3-ethynyl-1-azabicyclo[2.2.2]oct-3-yl acetate

Product 1

HCID 946095(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-olYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The acetate 49 (179 g, 0.926 mol) was treated with a solution of NaH (60% dispersion in oil, 100 mg, 2.7 mmol) in methanol (900 ml). After stirring for 2 hours at reflux, water (20 ml) was added and the solution concentrated. The residue was treated with ether and the white solid obtained was filtered off, dissolved in ethanol (2 L) and water (200 ml). The mixture was evaporated to dryness and dried under vacuum to give the (3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-ol 50 as a white solid (138 g, 98%).

Workup

  1. temperatureat reflux
  2. concentrationthe solution concentrated
  3. additionThe residue was treated with ether
  4. customthe white solid obtained
  5. filtrationwas filtered off
  6. dissolutiondissolved in ethanol (2 L)
  7. customThe mixture was evaporated to dryness
  8. customdried under vacuum

Sources & evidence

ORD record
ord-0bfe18b8a4d14bcab3be75587080dadd
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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