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

HRID 2358303ノート

反応式

HRID 2358303 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0cd9d79ac44b4a288aab6474ee817b91
出典データセット
uspto-grants-2010_07
特許番号
US07763614B2

反応ノート

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