Water → (S)-3-((S)-1-(4-bromophenyl)-ethyl)-6-(2,3-dihydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

HRID 470435Notes

Reaction equation

HRID 470435 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13](CC(C)=C)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=O)[CH3:9])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:31]CC1.C1COCC1.[CH3:40][C:41]([OH:44])([CH3:43])[CH3:42].[OH2:45]>[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:40][C:41]([OH:44])([CH3:43])[CH2:42][OH:31])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:45][C:11]2=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 46830455(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 59635738(S)-3-((S)-1-(4-bromophenyl)-ethyl)-6-(2,3-dihydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-oneYield 74.5%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (300 mg, 0.726 mmol), 4-methylmorpholine 4-oxide (195 mg, 1.44 mmol) in a mixture of H2O (6 mL), THF (30 mL) and t-BuOH (12 mL) was added osmium (VIII) oxide (4%, 0.231 mL) at 0° C. The mixture was stirred at rt overnight. The mixture was quenched with 3% NaHSO3 (15 mL×3) and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give the crude product (S)-3-((S)-1-(4-bromophenyl)-ethyl)-6-(2,3-dihydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (242 mg, 74.5%).

Workup

  1. customThe mixture was quenched with 3% NaHSO3 (15 mL×3)
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-78b35b55d9b74875be3456ce9c014335
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

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