tert-butyl (1R,5S)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate → tert-Butyl 3-hydroxy-8-azabicyclo(3.2.1)octane-8-carboxylate
Reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@@H:12]2[CH2:13][C:14]([CH2:16][C@H:9]1[CH2:10][CH2:11]2)=[O:15])=[O:7])([CH3:4])[CH3:3].[BH4-].[Na+]>CO>[C:2]([O:5][C:6]([N:8]1[CH:12]2[CH2:11][CH2:10][CH:9]1[CH2:16][CH:14]([OH:15])[CH2:13]2)=[O:7])([CH3:4])([CH3:1])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. cold solution of 2.00 g N-Boc-nortropinone in 50 mL of methanol was added portionwise 672 mg of sodium borohydride. The reaction mixture was stirred at 0° C. for 1 h. The solvent was evaporated, the crude product was taken up in dichloromethane and treated with sat. sodium bicarbonate solution. The phases were separated and the aqueous phase extracted twice with dichloromethane. The organic phases were combined, dried over magnesium sulfate and concentrated to give 3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (70) as diastereomeric mixture. Rt=1.11 min, 1.17 min (Method C). Detected mass: 128.0 (M-Boc+H+).
Workup
- customThe solvent was evaporated
- additiontreated with sat. sodium bicarbonate solution
- customThe phases were separated
- extractionthe aqueous phase extracted twice with dichloromethane
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-428b4812f99c4a638664e8baf52484d4
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772492B2
Reaction notes
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