Ozone → HCID 58109689, compound

HRID 2037487Notes

Reaction equation

HRID 2037487 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@@:12]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]=C)=[CH:23][CH:22]=2)[CH3:20])[CH2:14][CH2:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:35]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@@:12]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][OH:35])=[CH:23][CH:22]=2)[CH3:20])[CH2:14][CH2:13]1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 58109435HCID 58109435, compound

Product 1

HCID 58109689HCID 58109689, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (40 mg, 0.08 mmol) in CH2Cl2 (15 mL) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to move excess ozone. NaBH4 (12.2 mg, 0.32 mmol) was added to the mixture in portions at rt, and the mixture was stirred overnight at rt. The reaction was quenched by water, and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layer was combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product, which was purified by preparative TLC to give (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-((S)-1-(4-(hydroxylmethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 25%). 1H NMR (CDCl3): 0.00 (s, 4H), 0.09 (s, 2H), 0.87 (s, 8H), 1.28 (s, 4H), 1.53 (d, 3H), 1.98 (d, 2H), 3.53 (m, 2H), 4.25 (m, 1H), 4.98 (m, 1H), 4.61 (m, 1H), 5.71 (m, 1H), 6.90 (m, 1H), 7.12-7.38 (m, 10H).

Workup

  1. customThe system was then flushed with oxygen
  2. customThe reaction was quenched by water
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-380143e797b748068e3c04054dcb5be5
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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