Potassium Hydroxide → 3-Benzyl-3-azabicyclo[3.2.1]octan-6-ol

HRID 272614Notes

Reaction equation

HRID 272614 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([CH2:11][CH:12]2[O:16]C(=O)C)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO.O>[CH2:1]([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([CH2:11][CH:12]2[OH:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68806364Acetic acid 3-benzyl-3-aza-bicyclo[3.2.1]oct-6-yl ester

Product 1

HCID 598378273-Benzyl-3-azabicyclo[3.2.1]octan-6-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of acetic acid 3-benzyl-3-aza-bicyclo[3.2.1]oct-6-yl ester (8 mmol) in methanol (50 mL) and water (20 mL) was added potassium hydroxide (32 mmol). Reaction was stirred 18 h at room temperature. The methanol was removed in vacuo and product was extracted with aqueous dichloromethane (4×50 mL). The organic extracts were dried over MgSO4, filtered and stripped to provide a quantitative yield of an oil. APCl MS m/z 218.2 (M+H)+.

Workup

  1. customReaction
  2. customThe methanol was removed in vacuo and product
  3. extractionwas extracted with aqueous dichloromethane (4×50 mL)
  4. dry with materialThe organic extracts were dried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9df6a9e246a1457ea16a3ac13c93d701
Source dataset
uspto-grants-2008_11
Patent number
US07456177B2

Reaction notes

Loading…