tert-Butanol → 6-chloro-N-cyclopentyl-N-(2,3-dihydroxypropyl)pyridine-3-sulfonamide

HRID 2366079Notes

Reaction equation

HRID 2366079 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)CC=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:24]CC1.[CH3:28][C:29]([OH:32])(C)[CH3:30]>O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:28][CH:29]([OH:32])[CH2:30][OH:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6386tert-Butanol2×HCID 82029Methyl morpholine oxideHCID 610456036-chloro-N-cyclopentyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide

Product 1

HCID 866599586-chloro-N-cyclopentyl-N-(2,3-dihydroxypropyl)pyridine-3-sulfonamideYield 75%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 1.1 g (3.7 mmol) of 6-chloro-N-cyclopentyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide in 15 mL of a mixture (1/1) of tBuOH and water are added, at room temperature, 1.2 g (10.3 mmol) of NMO and 0.52 mL (0.04 mmol) of 2.5% OsO4 in tBuOH. Stirring is continued for 12 hours. The medium is then diluted with 200 mL of water and extracted with Et2O (2×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. 0.92 g of 6-chloro-N-cyclopentyl-N-(2,3-dihydroxypropyl)pyridine-3-sulfonamide is obtained in the form of a brown solid, which is used without further purification in the following step.

Workup

  1. extractionextracted with Et2O (2×100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e4ae56011fc144638b5432536c5443a1
Source dataset
uspto-grants-2014_04
Patent number
US08697731B2

Reaction notes

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