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

HRID 57312Notes

Reaction equation

HRID 57312 reaction equation
C(C12CCN(CC1)CC2)#N.Cl.[N:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2.CO>O1CCCC1>[N:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2.[N:12]12[CH2:19][CH2:18][C:15]([CH2:20][OH:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2

Participants

6

Reactant 3

HCID 887MethanolHCID 1412921-Azabicyclo[2.2.2]octane-4-carbonitrileHCID 667378251-Azabicyclo(2.2.2)octane-4-carboxylic acid hydrochloride

Product 2

HCID 1413111-Azabicyclo(2.2.2)octane-4-methanolHCID 13760939Quinuclidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Quinuclidin-4-yl)carboxylic acid was prepared from 4-cyanoquinuclidine (Oakwood Products) following the procedure of Grob and Renk, Helv. Chim. Acta, 37, 1681 (1954). 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-2bdc02a5f56741fd9fa9a53030450d2a
Source dataset
uspto-grants-2016_09
Patent number
US09434724B2

Reaction notes

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