Sodium Hydroxide → HCID 86692486, 화합물

HRID 1748535

반응식

HRID 1748535 반응식
[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

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 18522Dihydro-2-methyl-3(2H)-furanoneHCID 5049666Sodium triacetoxyborohydrideHCID 86692481HCID 86692481, 화합물

생성물 2

HCID 86692486HCID 86692486, 화합물HCID 86692487HCID 86692487, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f291bff8ffc641889e21e04f986dabc8
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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