Tetrabutylammonium Fluoride → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627127ノート

反応式

HRID 627127 の反応式
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH2:31][O:32][Si](C(C)(C)C)(C)C)[C:20]([CH3:40])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C@H:21]([CH2:31][OH:32])[C:20]([CH3:40])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 89852556(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate2 回

生成物 1

HCID 89852407(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate収率 79.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 80, 7.05 g, 11.79 mmol) in THF (100 mL) was charged with nitrogen and cooled in an ice-bath. Tetrabutylammonium fluoride in THF (14.15 mL, 14.15 mmol) was added to the solution and stirred at rt. The reaction mixture was evaporated and the crude product was loaded onto silica and purified via flash chromatography (30-100% EA/Hexanes, 40 g column), to obtain the desired product (4.52 g, 79%) as a pale yellow foam.

後処理

  1. temperaturecooled in an ice-bath
  2. customThe reaction mixture was evaporated
  3. custompurified via flash chromatography (30-100% EA/Hexanes, 40 g column)

出典と根拠

ORDレコード
ord-a9fae5c93a9a42e2882c69ddbe1f682e
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

読み込み中…