Sodium hydride → HCID 57459620、化合物

HRID 587642ノート

反応式

HRID 587642 の反応式
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][N:20]=1>C1COCC1.O>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([CH2:14][O:15][C:19]2[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 24758Sodium hydride2 回HCID 6933243-Bromo-2-chloropyridineHCID 11264156(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol2 回

生成物 1

HCID 57459620HCID 57459620、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of (1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-methanol (0.675 g, 3.019 mmol) [C.A.S. 158984-76-0] in dry THF (40 ml) cooled at 0° C., was added NaH (0.138 g, 3.622 mmol; 60% mineral oil). The resulting reaction mixture was stirred at 0° C. for 30 min. Then, a solution of 2-chloro-3-bromopyridine (0.58 g, 3.019 mmol) in dry THF (10 ml) was added and the mixture was heated in a sealed tube at 85° C. for 2 h. After cooling, additional (1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-methanol (0.675 g, 3.019 mmol), NaH (0.138 g, 3.622 mmol; 60% mineral oil) were added to the reaction mixture, which was then heated at 85° C. overnight. Then, after cooling, the mixture was diluted with water and extracted with EtOAc. The organic phase was separated, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate D58 (0.55 g, 50%).

後処理

  1. customThe resulting reaction mixture
  2. temperaturethe mixture was heated in a sealed tube at 85° C. for 2 h
  3. temperatureAfter cooling
  4. temperaturewas then heated at 85° C. overnight
  5. temperatureThen, after cooling
  6. extractionextracted with EtOAc
  7. customThe organic phase was separated
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo
  13. customto yield intermediate D58 (0.55 g, 50%)

出典と根拠

ORDレコード
ord-5ce54ed725c24f3e83c8636d38b065be
出典データセット
uspto-grants-2016_01
特許番号
US09226930B2

反応ノート

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