Hydrochloric Acid → HCID 57948675, compound
Reaction equation
[C:1]1([CH:7]2[C:12]3[C:13]([C:16]([N:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=O)=[N:14][O:15][C:11]=3[CH2:10][CH2:9][N:8]2C(OC(C)(C)C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.Cl>C1COCC1>[C:1]1([CH:7]2[C:12]3[C:13]([CH2:16][N:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)=[N:14][O:15][C:11]=3[CH2:10][CH2:9][NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To solution of tert-butyl 4-phenyl-3-(piperidine-1-carbonyl)-6,7-dihydro-isoxazolo[4,5-c]pyridine-5(4H)-carboxylate (3.16 mmol, 1.0 eq.) in THF (6.5 ml) was added BH3-DMS (1.2 ml, 4.0 eq.) and the reaction mixture was heated at 110° C. for 6 h. The mixture was cooled to room temperature and MeOH (5 ml) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for overnight. 6N HCl (1.5 ml) was added and the mixture was again heated at 110° C. for 2 h. The reaction mixture was concentrated to dryness and the residue was dissolved in dichloromethane, and basified with saturated sodium carbonate solution. The organic layer was separated, dried over sodium sulfate and the solvent was evaporated under reduced pressure to give the crude product which was purified by column chromatography. Yield: 40%. [The regiochemistry was assigned by NMR experiments (COSY; HSQC, HMBC).]
Workup
- temperatureThe mixture was cooled to room temperature
- temperaturethe mixture was again heated at 110° C. for 2 h
- concentrationThe reaction mixture was concentrated to dryness
- dissolutionthe residue was dissolved in dichloromethane
- customThe organic layer was separated
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-ea962a65a6fc4b7b98e1655160b4e5db
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268814B2
Reaction notes
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