Methanol → 1-Azabicyclo(2.2.2)octane-4-methanol

HRID 1641002Notes

Reaction equation

HRID 1641002 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][C:5]([C:10](O)=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.CO>O1CCCC1>[N:2]12[CH2:9][CH2:8][C:5]([CH2:10][OH:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 887MethanolHCID 667378251-Azabicyclo(2.2.2)octane-4-carboxylic acid hydrochloride

Product 1

HCID 1413111-Azabicyclo(2.2.2)octane-4-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of quinuclidine-4-carboxylic acid hydrochloride (100 mg, 0.523 mmol) in 3 mL of anhydrous tetrahydrofuran at 0° C. was added borane methylsulfide complex (42 mg, 0.553 mmol). The mixture was stirred at room temperature for 1 hr and heated to reflux overnight. The reaction was cooled to 0° C. and carefully treated with 1 mL of methanol. The solvent was then removed under reduced pressure to leave the desired alcohol. Yield 36 mg. MS (m/e): 141.

Workup

  1. additionwas added borane methylsulfide complex (42 mg, 0.553 mmol)
  2. temperatureheated
  3. temperatureto reflux overnight
  4. temperatureThe reaction was cooled to 0° C.
  5. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-caa33e356052463987ee09802fdb503f
Source dataset
uspto-grants-2012_02
Patent number
US08114891B2

Reaction notes

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