Triacetoxyperiodinane → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627161노트

반응식

HRID 627161 반응식
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([C:16](=[O:20])[N:17]([CH3:19])[CH3:18])[C@@H:13]([OH:21])[CH2:12][N:11]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([C:16](=[O:20])[N:17]([CH3:18])[CH3:19])[C:13](=[O:21])[CH2:12][N:11]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 89852488(2S,5R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate2회

생성물 1

HCID 89851837(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate수율 48.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(2S,5R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 133, 2.194 g, 5.29 mmol) in DCM (65 mL) was cooled in an ice-bath then Dess-Martin periodinane in DCM (26.5 mL, 7.94 mmol) was added and the reaction was stirred at rt overnight. The organic solution was washed with sat. Na2S2O3, sat. NaHCO3, brine, dried over MgSO4, filtered and evaporated. The crude product was purified via flash chromatography (10-75% EA/EtOAc) to obtain the desired product (1.050 g, 48.1%).

후처리

  1. washThe organic solution was washed with sat. Na2S2O3, sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified via flash chromatography (10-75% EA/EtOAc)

출처 및 근거

ORD 기록
ord-cb2c572e401c443fba3cdcda6891e71e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

반응 노트

불러오는 중…