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

HRID 657178ノート

反応式

HRID 657178 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b036f8cda359416f90a11ca4114b4407
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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