Réaction #473045

Équation de réaction

Sodium hydride

(1R,2R)-Cyclopentane-1,2-diol

2-Bromo-6-(bromomethyl)pyridine

→

title compound

(1R,2R)-2-[(6-Bromopyridin-2-yl)methoxy]cyclopentanol

Solvants

DMF

ether

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   Autrequenched with water
3. 3
   AutreAfter layer separation
4. 4
   Séchagethe organic layer was dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutrePurification of the crude residue by silica gel chromatography

Mode opératoire

Sodium hydride (0.48 mg, 11.96 mmol) was suspended in DMF (12.0 mL) and cooled to 0° C. (1R,2R)-Cyclopentane-1,2-diol (1.22 g, 11.96 mmol) was added and the reaction was stirred for 30 minutes. 2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (0.30 g, 1.20 mmol) was added and the reaction mixture was allowed to warm to room temperature overnight. The reaction was then diluted with ether and quenched with water. After layer separation, the organic layer was dried over magnesium sulfate, filtered and concentrated. Purification of the crude residue by silica gel chromatography afforded the title compound.

Source