1,4-Dioxane → HCID 15107109, compound

HRID 1651024Notes

Reaction equation

HRID 1651024 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:14]([CH:23]=C)[O:13][C:12]1([CH3:26])[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:27]1CCOCC1>O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:14]([CH:23]=[O:27])[O:13][C:12]1([CH3:26])[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 312751,4-Dioxane2×HCID 15107107HCID 15107107, compound

Product 1

HCID 15107109HCID 15107109, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

960 mg of (4S,5RS)-3-benzyloxycarbonyl-4-cyclohexylmethyl-5-ethenyl-2,2-dimethyloxazolidine was dissolved in 7 ml of dioxane, and 5 ml of dioxane solution containing 35 mg of osmium tetraoxide was added thereto, and reacted for 15 minutes at room temperture in the absence of light. The reaction mixture was diluted with 2.5 ml of water, and 8 ml of a solution containing 1.15 g of sodium periodide was dropwise added over a period of 40 minutes. After the completion of the addition, the mixture was stirred for 1.5 hours at room temperature. Insolubles were filtered off, and the filtrate was diluted with 100 ml of diethyl ether. The diluted filtrate was washed sequentially with a 5% sodium sulfide solution, water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 992 mg of (4S,5RS)-3-benzyloxycarbonyl-4-cyclohexylmethyl-5-formyl-2,2-dimethyloxazolidine as a colorless oily substance.

Workup

  1. additionwas added
  2. customreacted for 15 minutes at room temperture in the absence of light
  3. additionwas dropwise added over a period of 40 minutes
  4. additionAfter the completion of the addition
  5. filtrationInsolubles were filtered off
  6. additionthe filtrate was diluted with 100 ml of diethyl ether
  7. washThe diluted filtrate was washed sequentially with a 5% sodium sulfide solution, water
  8. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8a1d6a5932d840c6b2fa372644cba7aa
Source dataset
uspto-grants-1990_05
Patent number
US04927565

Reaction notes

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