(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627220노트

반응식

HRID 627220 반응식
[Si:1]([O:8][CH2:9][C@@H:10]1[C:15]([CH2:16][CH3:17])=[CH:14][C:13](=[O:18])[CH2:12][N:11]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OC[C@@H]1C=C(C)[C@H](O)CN1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C>>[Si:1]([O:8][CH2:9][C@@H:10]1[C:15]([CH2:16][CH3:17])=[CH:14][C@H:13]([OH:18])[CH2:12][N:11]1[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

3

반응물 2

HCID 89852241(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate2회HCID 89852486tert-Butyl (3S,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3-hydroxy-4-methyl-1,2,3,6-tetrahydropyridine-1-carboxylate

생성물 1

HCID 89852682(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate수율 100.3%

실험 절차

The title compound was prepared from (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 207, 5.146 g, 13.92 mmol) according to the procedure described for Intermediate 8, except the mixture was stirred at ambient temperature for 1 h. The mixture was concentrated and diluted with aqueous NH4Cl, water and EtOAc. The organic layer was separated and washed three times with brine, dried over Na2SO4, filtered and concentrated to afford the title compound (5.19 g, 100%) as a cloudy oil.

후처리

  1. concentrationThe mixture was concentrated
  2. additiondiluted with aqueous NH4Cl, water and EtOAc
  3. customThe organic layer was separated
  4. washwashed three times with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-51f0c8a30e7a4d1a985770e501bd5612
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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