Acetone → HCID 25182554, compound

HRID 2037421Notes

Reaction equation

HRID 2037421 reaction equation
C([C:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:9][C:8](=O)[N:7]([C:11]2[CH:12]=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])[CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)C=C.C[N+]1([O-])CC[O:35]CC1.[OH2:39].[CH3:40][C:41]([CH3:43])=[O:42]>O=[Os](=O)(=O)=O>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N:7]2[CH2:6][CH2:5][C:4]([CH2:40][CH:41]([OH:42])[CH2:43][OH:35])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:39][C:8]2=[O:9])[CH:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 82029Methyl morpholine oxideHCID 25182139HCID 25182139, compound

Product 1

HCID 25182554HCID 25182554, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 6-allyl-3-(2′,4′-difluorobiphenyl-3-yl)-6-phenyl-1,3-oxazinan-2-one (7.1 mg, 0.018 mmol) in acetone (0.5 mL) was added NMO.H2O (6 mg, 0.044 mmol), then OsO4 (10 μL, 2.5 wt % in 2-Me-2-propanol). The reaction was stirred overnight at rt. The solvent was evaporated and the residue was redissolved in EtOAc. The organic layer was washed with 10% aq Na2S2O3 (2×), 1M aq HCl (2×) and brine (1×). The organic layer was dried over Na2SO4, filtered, evaporated, and purified by prep HPLC to afford 3-(2′,4′-difluorobiphenyl-3-yl)-6-(2,3-dihydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (6.53 mg). LC-MS Method 1, m/z=440 (M+H)+. 1H NMR (CDCl3) 7.47-7.33 (m), 7.15-7.12 (m), 6.96-6.86 (m), 3.51 (br m), 3.37-3.26 (m), 2.69 (br m), 2.58-2.48 (m), 2.29-2.23 (m), 2.14 (d), 2.06 (d).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was redissolved in EtOAc
  3. washThe organic layer was washed with 10% aq Na2S2O3 (2×), 1M aq HCl (2×) and brine (1×)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by prep HPLC

Sources & evidence

ORD record
ord-efdf50b6e0e74043bb65cfed3626848a
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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