tert-Butanol → HCID 18918434, compound

HRID 2267697Notes

Reaction equation

HRID 2267697 reaction equation
[CH2:1]([O:8][C:9]([N:11]1CC=C[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:21]CC1.[C:25]([OH:29])([CH3:28])(C)[CH3:26].S(=O)(O)[O-].[Na+]>O.CC(C)=O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:26]([OH:21])[CH:25]([OH:29])[CH2:28]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 11458613Benzyl 5,6-dihydropyridine-1(2H)-carboxylateHCID 23665763Sodium Bisulfite

Product 1

HCID 18918434HCID 18918434, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

31 (3.63 g, 16.7 mmol) is dissolved in 16 ml of a 1:1 mixture of water and acetone. After addition of N-methyl-morpholine-N-oxide (2.9 g, 24.8 mmol), a 1% solution of osmium tetroxide in tert. Butanol (7.23 ml, 0.28 mmol) is added. The mixture is stirred at room temperature for 20 h. Then 70 ml of a saturated sodium bisulfite solution is added. After 15 min stirring at room temperature, the reaction mixture is extracted with ethyl acetate. The organic layers are dried over sodium sulphate and evaporated. The crude product, 4.7 g of a yellow oil, is purified by Flash-chromatography (silica gel, ethyl acetate).

Workup

  1. stirringAfter 15 min stirring at room temperature
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. dry with materialThe organic layers are dried over sodium sulphate
  4. customevaporated
  5. customThe crude product, 4.7 g of a yellow oil, is purified by Flash-chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-8792c5f392014b37932389224e2abc04
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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