Methyl morpholine oxide → HCID 9799516, compound

HRID 1724003Notes

Reaction equation

HRID 1724003 reaction equation
C[N+]1([O-])CCOCC1.[CH3:9][C:10]1([CH3:39])[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20]([O:34][Si](C)(C)C)=[CH:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)[CH:16]=2)[O:11]1>O.CC(C)=O.[Os](=O)(=O)(=O)=O>[CH3:9][C:10]1([CH3:39])[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20](=[O:34])[CH2:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)[CH:16]=2)[O:11]1

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 68649276HCID 68649276, compound

Product 1

HCID 9799516HCID 9799516, compoundYield 10.3%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A solution of osmium tetroxide (25% wt., 0.574 mL) and NMO (13.24 mg, 0.113 mmol) dissolved in water (0.27 mL) and acetone (0.48 mL) were cooled to −5° C. [1-(2,2-dimethyl-chroman-6-yl)-2-(3,4,5-trimethoxy-phenyl)-vinyloxy]-trimethyl-silane (50 mg, 0.113 mmol) dissolved in acetone (0.2 mL) was added dropwise to the cooled stirring solution. After completion of addition the reaction continued to stir at 0° C. After 3 h, the reaction was quenched with sodium hydrosulfite and florisil. The reaction mixture was filtered and the filtrate was concentrated. The crude material was purified using silica gel chromatography (4:1 pentane: ethyl acetate to 1:1 pentane ethyl acetate) to afford the desired compound (4.3 mg, 8%).

Workup

  1. additionwas added dropwise to the cooled
  2. additionAfter completion of addition the reaction
  3. stirringto stir at 0° C
  4. customthe reaction was quenched with sodium hydrosulfite and florisil
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe crude material was purified

Sources & evidence

ORD record
ord-e8fedc51666b4bf78c510cba35913f13
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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