Hydrochloric Acid → 6-(3-Hydroxypropyl)-6-phenyl-3-(2-phenylcyclopropyl)-1,3-oxazinan-2-one
Reaction equation
[CH2:1]([C:4]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([CH:11]2[CH2:13][CH:12]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:30]CC1.[OH-].[Na+].OO.Cl>C1COCC1.O>[OH:30][CH2:3][CH2:2][CH2:1][C:4]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:9][C:8](=[O:10])[N:7]([CH:11]2[CH2:13][CH:12]2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:6][CH2:5]1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 6-allyl-6-phenyl-3-(2-phenylcyclopropyl)-1,3-oxazinan-2-one (200 mg, 0.60 mmol) in dry THF (5 mL) was added dropwise 1 M of BH3/THF (1.8 mL, 1.8 mmol) at 0° C. under N2. After stirring at rt for 2 h, the reaction mixture was cooled to 0° C. again, and water (0.1 mL), 3 M of aqueous NaOH solution (0.1 mL), and 30% H2O2 (0.3 mL) were added sequentially. After the mixture was stirred at rt for another 2 h, 1 N aqueous HCl (0.5 mL) was added. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative TLC followed by preparative HPLC to afford two isomers.
Workup
- temperaturethe reaction mixture was cooled to 0° C. again
- stirringAfter the mixture was stirred at rt for another 2 h
- extractionThe mixture was extracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e048d400e08b486fb005969281dc8c57
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487094B2
Reaction notes
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