Water → (R)-N-(5-(1,2-Dihydroxy-ethyl)-pyrdin-2-yl)-2,2-dimethylpropionamide

HRID 1596499Notes

Reaction equation

HRID 1596499 reaction equation
C([OH:5])(C)(C)C.[CH:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][CH:13]=1)=[CH2:7].S([O-])([O-])=O.[Na+].[Na+].[OH2:27]>>[OH:27][C@H:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][CH:13]=1)[CH2:7][OH:5]

Participants

5

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 217020792,2-Dimethyl-N-(5-vinylpyridin-2-yl)-propionamide

Product 1

HCID 15540846(R)-N-(5-(1,2-Dihydroxy-ethyl)-pyrdin-2-yl)-2,2-dimethylpropionamideYield 96%

Conditions

Temperature
5 °C

Procedure

A suspension of AD-Mix-B® (1.40 g) in water (5 ml) and t-butanol (5 ml) was cooled to 5° C. and N-(5-vinyl-pyridin-2-yl)-2,2-dimethylpropionamide (0.204 g, 1.0 mmol) was added. The mixture was stirred at 5° C. for 18 hours. The reaction mixture was then treated with sodium sulfite (3.0 g), stirred for 30 minutes and then extracted with dichloromethane. The dichloromethane extract was washed with water and brine and then dried and evaporated to afford 0.230 g (96%) of the title product as colorless crystals. mp 105-106° C. 1H NMR (CDCl3): δ=8.21 (br, 1 H); 8.10 (m, 2 H); 7.61 (d of d, 1 H); 4.70 (m, 1 H); 3.64 (m, 1 H); 3.57 (m, 1 H); 1.25 (s, 9 H). MS (Cl): m/z=239 (M+H+).

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with dichloromethane
  3. extractionThe dichloromethane extract
  4. washwas washed with water and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-da8f4d6ee55c4ce79dccdf2e4a2aee17
Source dataset
uspto-grants-2001_09
Patent number
US06291489B1

Reaction notes

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