Hydrochloric Acid → HCID 42642393, compound

HRID 403595Notes

Reaction equation

HRID 403595 reaction equation
[CH2:1]([C:4]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:9][C:8](=[O:10])[N:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:25]CC1.[OH-].[Na+].OO.Cl>C1COCC1.O>[C:11]([N:7]1[CH2:6][CH2:5][C:4]([CH2:1][CH2:2][CH2:3][OH:25])([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:9][C:8]1=[O:10])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 58485274HCID 58485274, compound

Product 1

HCID 42642393HCID 42642393, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-allyl-3-tert-butyl-6-phenyl-1,3-oxazinan-2-one (400 mg, 1.46 mmol) in dry THF (10 mL) was added dropwise 1 M of BH3/THF (4.5 mL, 4.40 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 aq 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 aq HCl (1.5 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 chiral HPLC to afford two isomers of 3-tert-butyl-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C. again
  2. stirringAfter the mixture was stirred at rt for another 2 h
  3. extractionThe mixture was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-5b74c31a0421410a962b813868fdd102
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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