Ethyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate → 3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][C:9](=[O:14])[CH2:10]2)=[O:5])[CH3:2]>CO.[Ni]>[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([OH:14])[CH2:10]2)=[O:5])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (3.0 g, 15.23 mmol) in methanol (20 mL) was added 5 mL Raney Nickel (50% aq slurry). The resultant mixture was degassed and charged with hydrogen (g) three times, heated to 70° C. and stirred for 12 hrs. The suspension was filtered through celite, and concentrated to provide a white solid (3.0 g, 100%). 1H NMR (300 MHz, CDCl3) δ ppm 1.25 (t, J=7.0 Hz, 3H), 1.57 (m, 2H), 1.72 (app dd, J=1.4, 15.1 Hz, 2H), 1.94 (m, 2H), 2.12 (m 4H), 4.13 (q, J=7.1 Hz, 2H), 4.25 (m, 2H); MS (ESI+Q1MS) m/z 200 [M+H]+
Workup
- customThe resultant mixture was degassed
- additioncharged with hydrogen (g) three times
- filtrationThe suspension was filtered through celite
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f897731760af4075b64b13c09cc3d29f
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921821B2
Reaction notes
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