Hydrogen Peroxide → HCID 67998413, compound

HRID 1426005Notes

Reaction equation

HRID 1426005 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C:13]([CH2:21][CH:22]3[CH2:24][CH2:23]3)([CH2:16][C:17]3([CH3:20])[CH2:19][O:18]3)[O:12][C:11]2=[O:25])[CH3:9])=[CH:4][CH:3]=1.OO>O1CCCC1.COC(C)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([CH2:21][CH:22]3[CH2:24][CH2:23]3)([CH2:16][C:17]([OH:18])([CH3:20])[CH3:19])[O:12][C:11]2=[O:25])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 86696139HCID 86696139, compound

Product 1

HCID 67998413HCID 67998413, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
2.5 °C

Procedure

LiBHEt3 solution (1 mol/L, 34 mL) was added dropwise to a solution of 3-[(S)-1-(4-bromophenyl)ethyl]-6-(cyclopropylmethyl)-6-[(2-methyloxiran-2-yl)methyl]-1,3-oxazinan-2-one (1.40 g) in tetrahydrofuran (200 mL) at 0° C. The resulting solution was stirred at 2-3° C. for 1.5 h and then at room temperature for another 3 h. 30% aqueous H2O2 solution (30 mL) was added dropwise at 0° C. and the mixture was diluted with tert-butyl methyl ether (200 mL). The mixture was washed with 3% aqueous Na2S2O3 solution and saturated aqueous NaHCO3 solution (4×100 mL) and dried (Na2SO4). The solvent was evaporated and the residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 1:1→3:1) to afford the title compound; besides, the diastereomer, 3-[(S)-1-(4-bromophenyl)ethyl]-(R)-6-(cyclopropylmethyl)-6-(2-hydroxy-2-methylpropyl)-1,3-oxazinan-2-one was also isolated (0.40 g, 29% yield). Yield: 0.55 g (40% of theory).

Workup

  1. waitat room temperature for another 3 h
  2. washThe mixture was washed with 3% aqueous Na2S2O3 solution and saturated aqueous NaHCO3 solution (4×100 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customthe residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 1:1→3:1)

Sources & evidence

ORD record
ord-ee1df6de72004895ad9a442bf7140e92
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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