Reaktion #473045

Reaktionsgleichung

Sodium hydride

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

2-Bromo-6-(bromomethyl)pyridine

→

title compound

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

Lösungsmittel

DMF

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigequenched with water
3. 3
   SonstigeAfter layer separation
4. 4
   Trocknenthe organic layer was dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigePurification of the crude residue by silica gel chromatography

Vorschrift

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.

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