Ozone → HCID 66856938, compound

HRID 2037499Notes

Reaction equation

HRID 2037499 reaction equation
[CH2:1]([C:4]1([CH:27]([CH3:29])[CH3:28])[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=C.[O:30]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C:4]([CH2:1][CH2:2][OH:30])([CH:27]([CH3:29])[CH3:28])[O:9][C:8]2=[O:10])[CH3:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 58109711HCID 58109711, compound

Product 1

HCID 66856938HCID 66856938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-allyl-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-isopropyl-1,3-oxazinan-2-one (60 mg, crude) 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 (29 mg, 0.75 mmol) was added to the mixture in portions at rt. 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 the crude product, which was purified by preparative TLC to give two isomers.

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-54fd659b67f841d7859cd26384786873
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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