Hydrochloric Acid → HCID 58109571, compound

HRID 2037476Notes

Reaction equation

HRID 2037476 reaction equation
[CH2:1]([C:4]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:29]CC1.[OH-].[Na+].OO.Cl>C1COCC1.O>[OH:29][CH2:3][CH2:2][CH2:1][C:4]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:6][CH2:5]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 66856865HCID 66856865, compound

Product 1

HCID 58109571HCID 58109571, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-allyl-3-phenethyl-6-phenyl-[1,3]oxazinan-2-one (100 mg, 0.31 mmol) in dry THF (4 mL) was added dropwise BH3.THF (0.6 mL, 0.62 mmol, 1 M) at 0° C. After 2 h at rt, the reaction mixture was cooled to 0° C., and water (1 mL), aqueous NaOH (1 mL, 3 M) and H2O2 (0.5 mL, 30%) were successively added. The mixture was stirred for 2-3 h at rt, and then diluted with water (8 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 (3×6 mL). The combined organic layers were washed with a saturated aqueous NaHCO3 solution (10 mL) and brine (10 mL), dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by preparative TLC to afford two isomers of 6-(3-hydroxypropyl)-3-phenethyl-6-phenyl-1,3-oxazinan-2-one.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (3×6 mL)
  3. washThe combined organic layers were washed with a saturated aqueous NaHCO3 solution (10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product, which
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-02a79eb950684225afcb57778ba04428
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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