Ozone → HCID 25182557, compound

HRID 2037416Notes

Reaction equation

HRID 2037416 reaction equation
[CH2:1]([C:4]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=2)[CH2:6][CH2:5]1)[CH:2]=C.[O:24]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl>[Br:17][C:13]1[CH:12]=[C:11]([N:7]2[CH2:6][CH2:5][C:4]([CH2:1][CH2:2][OH:24])([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:9][C:8]2=[O:10])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 25182140HCID 25182140, compound

Product 1

HCID 25182557HCID 25182557, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-allyl-3-(3-bromophenyl)-6-phenyl-1,3-oxazinan-2-one (200 mg, 0.54 mmol) in dry CH2Cl2 (10 mL) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to remove excess ozone. NaBH4 (207 mg, 5.4 mmol) was added to the mixture in portions at −20° C. The mixture was stirred overnight at rt. The mixture was quenched with water and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-(3-bromophenyl)-6-(2-hydroxyethyl)-6-phenyl-1,3-oxazinan-2-one (75 mg, 37%). 1H NMR (400 MHz, CDCl3): δ=2.12-2.30 (m, 2H), 2.47 (m, 2H), 3.19 (m, 1H), 3.40 (m, 1H), 3.53 (m, 1H), 3.76 (m, 1H), 7.06 (m, 1H), 7.13 (m, 1H), 7.22 (m, 1H), 7.25-7.40 (m, 6H).

Workup

  1. customThe system was then flushed with oxygen
  2. customto remove excess ozone
  3. customThe mixture was quenched with water
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-60a86e65993e49c18e5c76a370ec2b3c
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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