Hydrogen Peroxide → HCID 66899040, compound

HRID 1422660Notes

Reaction equation

HRID 1422660 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:11]2[CH2:16][CH2:15][C:14]([CH2:23][C:24]3([CH3:27])[CH2:26][O:25]3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:13][C:12]2=[O:28])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.OO.[CH2:31]1COCC1>CC(OC)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:11]2[CH2:16][CH2:15][C:14]([CH2:23][C:24]([OH:25])([CH2:26][CH3:31])[CH3:27])([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:13][C:12]2=[O:28])([CH3:9])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 86669143HCID 86669143, compound

Product 1

HCID 66899040HCID 66899040, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 3-(2-(4-bromophenyl)propan-2-yl)-6-((2-methyloxiran-2-yl)methyl)-6-phenyl-1,3-oxazinan-2-one (57 mg, 128.4 μmol) in THF (10 mL) was added dropwise LiBEt3H (642 mL, 642 μmol) at 0° C. under nitrogen. The resulting mixture was stirred at 10° C. for 2 h. The reaction solution was cooled to 0° C. Hydrogen peroxide (10 mL) was added dropwise while maintain the temperature below 25° C. The resulting mixture was diluted with MTBE (50 mL), washed with water (50 mL) and 30 wt % aqueous sodium thiosulfate (50 mL×3). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative HPLC to afford 3-(2-(4-bromophenyl) propan-2-yl)-6-(2-hyroxy-2-ethylpropyl)-6-phenyl-1,3-oxazinan-2-one. 1H NMR: (CDCl3) δ 7.45-7.26 (m, 7H), 6.94-6.92 (d, 2H), 3.27-3.24 (m, 1H), 2.85-2.78 (m, 1H), 2.41-2.30 (m, 2H), 2.22 (m, 3H), 1.65 (s, 3H), 1.47 (s, 3H), 1.15 (s, 3H), 1.03 (s, 3H); LC-MS Method 2 tR=1.35 min, m/z=448, 446.

Workup

  1. temperatureThe reaction solution was cooled to 0° C
  2. temperaturewhile maintain the temperature below 25° C
  3. washwashed with water (50 mL) and 30 wt % aqueous sodium thiosulfate (50 mL×3)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9ce4d9a0b3ab4195baa0eb504750fc38
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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