Water → 8-Benzyl-8-azabicyclo[3.2.1]octan-3-ol

HRID 1269859Notes

Reaction equation

HRID 1269859 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[O:16])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.O>O1CCCC1>[CH2:1]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([OH:16])[CH2:10]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-oneHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 147627438-Benzyl-8-azabicyclo[3.2.1]octan-3-olYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (16 ml) was dissolved 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (1.0 g, 4.64 mmol), and a 1M-diisobutylaluminum hydride/toluene solution (11.6 ml, 11.6 mmol) was added dropwise thereto at −78° C. over a period of 10 minutes and stirred for another 1 hour. Water was added dropwise thereto to quench the excess reactants, and the resulting mixture was separated by the addition of a 2N-aqueous hydrochloric acid solution and ethyl acetate. The aqueous layer was adjusted to pH 10 or lower with a 2N-aqueous sodium hydroxide solution and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated to obtain 8-benzyl-8-azabicyclo[3.2.1]octan-3-ol (886 mg, 88%).

Workup

  1. customto quench the excess reactants
  2. customthe resulting mixture was separated by the addition of a 2N-aqueous hydrochloric acid solution and ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38ff549585a34a1286e191067358654a
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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