Sodium borohydride → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627162ノート

反応式

HRID 627162 の反応式
O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[Si:12]([O:19][CH2:20][C@@H:21]1[CH:26]=[C:25]([C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[C:24](=[O:32])[CH2:23][N:22]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[BH4-].[Na+]>CO>[Si:12]([O:19][CH2:20][C@@H:21]1[CH:26]=[C:25]([C:27](=[O:31])[N:28]([CH3:29])[CH3:30])[C@H:24]([OH:32])[CH2:23][N:22]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 89851837(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate2 回

生成物 1

HCID 89851842(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylate収率 98.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of cerium(III) chloride heptahydrate (0.948 g, 2.54 mmol) and (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 134, 1.05 g, 2.54 mmol) in 1 mL MeOH at 0° C., sodium tetrahydroborate (0.096 g, 2.54 mmol) was added as a solid. The mixture was stirred at ambient temp for 15 minutes. The mixture was concentrated and diluted with NH4Cl (aq), H2O and ether. The ether layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product (1.034 g, 98%) as a beige solid.

後処理

  1. concentrationThe mixture was concentrated
  2. additiondiluted with NH4Cl (aq), H2O and ether
  3. customThe ether layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-5ae751dbdb8642568babc54be59ceea8
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…