Hydrogen Peroxide → HCID 59627224, compound

HRID 1523261Notes

Reaction equation

HRID 1523261 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]([CH2:22][C:23]3([CH3:26])[CH2:25][O:24]3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.[Li+].[B-](CC)(CC)CC.OO>O1CCCC1.O.C(OC)(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]([CH2:22][C:23]([OH:24])([CH3:25])[CH3:26])([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 23712863Lithium triethylborohydrideHCID 59627214HCID 59627214, compound

Product 1

HCID 59627224HCID 59627224, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of (4S)-1-((S)-1-(4-bromophenyl)ethyl)-4-((2-methyloxiran-2-yl)methyl)-4-phenyltetrahydropyrimidin-2(1H)-one (0.61 g, 1.42 mmol) in anhydrous tetrahydrofuran (5 mL) was added to Super Hydride (2.56 mL, 2.56 mmol) at 0-5° C. The addition is exothermic and addition was controlled to maintain Tint=<8° C. The mixture was stirred for 2 h at 0-5° C. and allowed to warm to 10-15 0° C. over 3 h. A solution of hydrogen peroxide (5 mL of a 30 wt % aqueous solution diluted with 50 mL of water) was added. The temperature was controlled to maintain Tint=<25° C. The resulting solution was diluted with methyl tert-butyl ether (MTBE) (200 mL) and washed with water (200 mL) followed by 30 wt % aq solution of sodium thiosulfate (300 mL). The organic solution was dried over Na2SO4, filtered and then concentrated to dryness. The residue was purified by column to afford (S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-hydroxy-2-methylpropyl)-4-phenyltetrahydropyrimidin-2(1H)-one (0.5 g, Yield: 82%). 1H NMR (MeOD): 0.58 (s, 3H), 1.17 (s, 3H), 1.44-1.46 (d, 3H), 1.90-1.94 (m, 2H), 2.05-2.08 (m, 1H), 2.16-2.18 (m, 1H), 2.24-2.27 (m, 1H), 2.83-2.86 (m, 1H), 5.65-5.67 (m, 1H), 7.04-7.06 (m, 2H), 7.22-7.23 (m, 1H), 7.27-7.33 (m, 6H). LC-MS Method 2 tR=1.296 min, m/z=433.

Workup

  1. additionThe addition
  2. additionaddition
  3. temperatureto maintain Tint=<8° C
  4. temperatureto warm to 10-15 0° C. over 3 h
  5. additionwas added
  6. temperatureto maintain Tint=<25° C
  7. washwashed with water (200 mL)
  8. dry with materialThe organic solution was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customThe residue was purified by column

Sources & evidence

ORD record
ord-2a9461703880496b88e9fcfde1d04b68
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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