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

HRID 611613Notes

Reaction equation

HRID 611613 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-dimethylpropionamide

Conditions

Temperature
5 °C

Procedure

A suspension of AD-Mix-B® (1.40 9) 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.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-d35b7a7561724eb387e63bbdbd1c7c34
Source dataset
uspto-grants-1999_12
Patent number
US06001856

Reaction notes

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