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

HRID 627161ノート

反応式

HRID 627161 の反応式
[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]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 89852488(2S,5R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-cb2c572e401c443fba3cdcda6891e71e
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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