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

HRID 657178Notes

Reaction equation

HRID 657178 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b036f8cda359416f90a11ca4114b4407
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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