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

HRID 385863

反応式

HRID 385863 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c3e83f6eb9c4302b1ffec8076b997d3
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

関連ノート

読み込み中…