Sodium Hydroxide → HCID 86692486、化合物

HRID 1748535

反応式

HRID 1748535 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)=[N:6][CH:7]=1.[CH3:15][CH:16]1[C:20](=O)[CH2:19][CH2:18][O:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([C:8]2[CH2:9][CH2:10][N:11]([C@H:20]3[CH2:19][CH2:18][O:17][C@H:16]3[CH3:15])[CH2:12][CH:13]=2)=[N:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([C:8]2[CH2:9][CH2:10][N:11]([C@@H:20]3[CH2:19][CH2:18][O:17][C@H:16]3[CH3:15])[CH2:12][CH:13]=2)=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 18522Dihydro-2-methyl-3(2H)-furanoneHCID 5049666Sodium triacetoxyborohydrideHCID 86692481HCID 86692481、化合物

生成物 2

HCID 86692486HCID 86692486、化合物HCID 86692487HCID 86692487、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-bromo-3-methyl-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine (2.26 g) described in Reference Example 109 (2) and 2-methyltetrahydrofuran-3-one (1.1 ml) in dichloromethane (25 ml) was added sodium triacetoxyborohydride (2.77 g), and stirred at room temperature for 6 hours. To the reaction solution was added 1 N aqueous solution of sodium hydroxide, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give cis-4-(5-bromo-3-methyl-pyridin-2-yl)-1-(2-methyltetrahydrofuran-3-yl)-1,2,3,6-tetrahydropyridine (2.43 g) and trans-4-(5-bromo-3-methylpyridin-2-yl)-1-(2-methyltetrahydrofuran-3-yl)-1,2,3,6-tetrahydropyridine (193 mg) as brown oils respectively. MS (ESI) m/z: 337, 339 (M+H)+.

後処理

  1. extractionextracted with chloroform
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-f291bff8ffc641889e21e04f986dabc8
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

関連ノート

読み込み中…