Hydrochloric Acid → HCID 58109540, compound
Reaction equation
[CH2:1]([C:4]1([CH:20]([CH3:22])[CH3:21])[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:27]CC1.[OH-].[Na+].OO.Cl>C1COCC1.O>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C:4]([CH2:1][CH2:2][CH2:3][OH:27])([CH:20]([CH3:22])[CH3:21])[O:9][C:8]2=[O:10])[CH3:12])=[CH:18][CH:17]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 6-allyl-3-((S)-1-(4-chlorophenyl)ethyl)-6-isopropyl-1,3-oxazinan-2-one (45 mg, 0.14 mmol) in dry THF (5 mL) was added dropwise 1 M BH3.THF (0.28 mL, 0.28 mmol) at 0° C. After 2 h at rt, the reaction mixture was cooled to 0° C., and water (1 mL), 3 M aqueous NaOH (1 mL, 3 M) and 30% H2O2 (0.5 mL) were successively added. The mixture was stirred for 2-3 h at rt and was then diluted with water (6 mL). The pH of the mixture was adjusted to 6-7 with 0.5 N HCl. The layers were separated, and the aqueous phase was extracted with EtOAc (3×5 mL). The combined organic layers were washed with a saturated aqueous NaHCO3 solution (8 mL) and brine (8 mL), dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by preparative TLC followed by preparative HPLC to afford two isomers.
Workup
- customThe layers were separated
- extractionthe aqueous phase was extracted with EtOAc (3×5 mL)
- washThe combined organic layers were washed with a saturated aqueous NaHCO3 solution (8 mL) and brine (8 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-99d87d28c75043b790a364347b4a088e
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575156B2
Reaction notes
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