Sodium Sulfite → 2-(2,3-Dihydroxypropyl)-6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

HRID 2358303Notes

Reaction equation

HRID 2358303 reaction equation
[CH2:1]([N:4]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:22][CH3:23])[CH:10]=2)[C:5]1=[O:24])[CH:2]=C.C[N+]1([O-])CC[O:29]CC1.[C:33]([O-:36])(O)=O.[Na+].[O-]S([O-])=O.[Na+].[Na+]>CC(C)=O.O.O=[Os](=O)(=O)=O>[OH:29][CH:2]([CH2:33][OH:36])[CH2:1][N:4]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:22][CH3:23])[CH:10]=2)[C:5]1=[O:24]

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 111745252-Allyl-6-methoxy-1-oxo-4-phenyl-1.2-dihydroisoquinoline-3-carbonitrile

Product 1

HCID 114053982-(2,3-Dihydroxypropyl)-6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Compound 88 (261 mg, 0.83 mmol) was dissolved in 24 mL of acetone and 10 mL of water. OsO4 (Aldrich, 2.5% in 2-Me-2-propanol, 1.04 mL) was added then NMO (116 mg, 1 mmol). The resulting mixture was stir at RT overnight then diluted with 1:1 sat NaHCO3/sat Na2SO3. It was partitioned between EtOAc and aq NaHCO3, then the organic phase was washed once with brine. The combined aqueous phases were washed once with EtOAc. Drying (Na2SO4) and concentration gave the title compound 89 as a light brown solid.

Workup

  1. additionthen diluted with 1:1
  2. customIt was partitioned between EtOAc and aq NaHCO3
  3. washthe organic phase was washed once with brine
  4. washThe combined aqueous phases were washed once with EtOAc
  5. customDrying
  6. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-0cd9d79ac44b4a288aab6474ee817b91
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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