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

HRID 385863

반응식

HRID 385863 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c3e83f6eb9c4302b1ffec8076b997d3
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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