Acetone → HCID 68489938, compound

HRID 1877995Notes

Reaction equation

HRID 1877995 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH:14]3[CH2:16][CH2:15]3)([CH:12]=C)[C:6]=2[CH:17]=1.[O:18]=[O+][O-].[BH4-].[Na+].CC(C)=O>ClCCl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH:14]3[CH2:16][CH2:15]3)([CH2:12][OH:18])[C:6]=2[CH:17]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 24823Ozone2×HCID 4311764Sodium borohydrideHCID 68489914HCID 68489914, compound

Product 1

HCID 68489938HCID 68489938, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Chloro-4-cyclopropyl-4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (590 mg, 2.36 mmol) was dissolved in dichloromethane (2.5 mL) and methanol (2.5 mL), and the resulting solution was stirred at −78° C. in an ozone atmospher. After it was confirmed by thin-layer chromatography that the raw materials disappeared, the ozone atmospher was replaced by a nitrogen atmospher, and the solution was stirred for 5 minutes. The temperature of the reaction solution was raised to 0° C., and sodium borohydride (26.8 mg, 7.1 mmol) was added thereto. The reaction solution was stirred at 0° C. for 30 minutes, and then, acetone was added thereto to stop the reaction. After the solvent was evaporated under reduced pressure, water (50 mL) and 1 N hydrochloric acid were added to the residue and the pH thereof was adjusted to about 4, and then, the solution was stirred at room temperature. The resulting white solid was collected by filtration, washed with water and then dried under reduced pressure, whereby the objective compound (487 mg, 81%) was obtained.

Workup

  1. stirringThe reaction solution was stirred at 0° C. for 30 minutes
  2. customthe reaction
  3. customAfter the solvent was evaporated under reduced pressure, water (50 mL) and 1 N hydrochloric acid
  4. additionwere added to the residue
  5. stirringthe solution was stirred at room temperature
  6. filtrationThe resulting white solid was collected by filtration
  7. washwashed with water
  8. dry with materialdried under reduced pressure, whereby the objective compound (487 mg, 81%)
  9. customwas obtained

Sources & evidence

ORD record
ord-b8086c323f66494b9a47427ca1501f5f
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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