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

HRID 627162노트

반응식

HRID 627162 반응식
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]

참가 물질

5

반응물 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 89851837(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ae751dbdb8642568babc54be59ceea8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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