Sodium Sulfite → Racemic 1,1-dimethylethyl ({1-[2-(7-fluoro-2-oxo-1(2H)-quinoxalinyl)ethyl]-4-oxo-3-piperidinyl}methyl)carbamate

HRID 657178노트

반응식

HRID 657178 반응식
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:30])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH:16]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:15]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:30])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][C:17](=[O:20])[CH:16]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:15]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 91235852racemic 1,1-dimethylethyl ({1-[2-(7-fluoro-2-oxo-1(2H)-quinoxalinyl)ethyl]-4-hydroxy-3-piperidinyl}methyl)carbamate

생성물 1

HCID 91469554Racemic 1,1-dimethylethyl ({1-[2-(7-fluoro-2-oxo-1(2H)-quinoxalinyl)ethyl]-4-oxo-3-piperidinyl}methyl)carbamate수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of racemic 1,1-dimethylethyl ({1-[2-(7-fluoro-2-oxo-1(2H)-quinoxalinyl)ethyl]-4-hydroxy-3-piperidinyl}methyl)carbamate (2.0 g, 4.76 mmol) in dry dichloromethane (120 mL) was added Dess-Martin periodinane (1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one, 3.03 g, 7.12 mmol) in portions over 5 min. The mixture was stirred for 1 h, then 10% aqueous sodium sulphite (70 mL) and aqueous sodium bicarbonate (60 mL) were added and stirring continued for 0.5 h. The phases were separated and the aqueous phase was extracted twice with dichloromethane. The organic fractions were dried and evaporated and the residue was chromatographed on silica, eluting with 50-100% ethyl acetate/hexane, to give the product (1.35 g, 68%).

후처리

  1. stirringstirring
  2. waitcontinued for 0.5 h
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with dichloromethane
  5. customThe organic fractions were dried
  6. customevaporated
  7. customthe residue was chromatographed on silica
  8. washeluting with 50-100% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-b036f8cda359416f90a11ca4114b4407
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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