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

HRID 2358303노트

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HRID 2358303 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0cd9d79ac44b4a288aab6474ee817b91
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07763614B2

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