Ammonium Chloride → (4H,6H,7H-pyrazolo(3,2-c)(1,4)oxazin-2-yl)methanol
Reaction equation
[N:1]1[N:9]2[C:4]([CH2:5][O:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[C:10](OCC)=[O:11].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C(Cl)Cl>[N:1]1[N:9]2[C:4]([CH2:5][O:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[CH2:10][OH:11]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of ethyl 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine-2-carboxylate (1.57 g, 8.0 mmol) in methylene chloride (30 ml) was added 24 ml of a 1.0 M solution of diisobutylaluminum hydride in methylene chloride at 0° C., under nitrogen. After stirring for 0.5 hr at 0° C., the mixture was warmed to room temperature for 2 hr. It was then treated with 30 ml of saturated ammonium chloride solution and extracted with ethyl acetate. The organic solution was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give 1.27 g of a colorless oil; MS (ESI) m/z 155.3 (M+H).
Workup
- temperaturethe mixture was warmed to room temperature for 2 hr
- extractionextracted with ethyl acetate
- washThe organic solution was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-85f5c208a895419c8a578bd8d2cac6b1
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812014B2
Reaction notes
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