Methanol → (1S,3R,4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylic acid
Reaction equation
[C:1]1([C@@H:7]([N:9]2[C@@H:14]([C:15]([O:17]CC)=[O:16])[C@H:13]3[CH2:20][C@@H:10]2[CH2:11][CH2:12]3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+]>O1CCCC1>[C:1]1([C@@H:7]([N:9]2[C@@H:14]([C:15]([OH:17])=[O:16])[C@H:13]3[CH2:20][C@@H:10]2[CH2:11][CH2:12]3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of ethyl (1S, 3R, 4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate (601 mg, 2.20 mmol) in tetrahydrofuran (12 ml)-methanol (6 ml) was added 1N sodium hydroxide (12 ml) and the mixture was stirred at 65° C. for 21 hours. The reaction mixture was neutralized and the water phase was concentrated. The residue was dissolved in chloroform and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (0–15% methanol/chloroform), to give (1S, 3R, 4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylic acid (445 mg, 83%).
Workup
- concentrationthe water phase was concentrated
- dissolutionThe residue was dissolved in chloroform
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated
- customthe residue was purified by silica gel column chromatography (0–15% methanol/chloroform)
Sources & evidence
- ORD record
- ord-f3b3c21c94eb43e3bfc69c2b02bb8df1
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176217B2
Reaction notes
Loading…