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

HRID 385863

Reaction equation

HRID 385863 reaction equation
[H-].[Na+].[C@@H:3]1([OH:9])[CH2:7][CH2:6][CH2:5][C@H:4]1[OH:8].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]Br)[N:12]=1>CN(C=O)C.CCOCC>[Br:10][C:11]1[N:12]=[C:13]([CH2:17][O:8][C@@H:4]2[CH2:5][CH2:6][CH2:7][C@H:3]2[OH:9])[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 225711trans-1,2-CyclopentanediolHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 59526405(1R,2R)-2-[(6-Bromopyridin-2-yl)methoxy]cyclopentanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. additionwas added
  2. customquenched with water
  3. customAfter layer separation
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude residue by silica gel chromatography

Sources & evidence

ORD record
ord-9c3e83f6eb9c4302b1ffec8076b997d3
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

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