N-Methylmorpholine N-oxide monohydrate → Methyl 2-(3-oxocyclohexyl)acetate

HRID 420766ノート

反応式

HRID 420766 の反応式
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([OH:11])[CH2:6]1.O.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1

参加物

5

反応物 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 57577344Rac-cis (3-hydroxy-cyclohexyl)-acetic acid methyl ester

生成物 1

HCID 566095Methyl 2-(3-oxocyclohexyl)acetate

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

rac-cis-(3-Hydroxy-cyclohexyl)-acetic acid methyl ester (500 mg, 2.90 mmol) (Example 5, step 1) was dissolved in 2 ml dichloromethane and tetrapropylammonium perruthenate [TPAP] (102 mg, 0.29 mmol) and 4-methylmorpholine oxide monohydrate (590 mg, 4.35 mmol) were added. The reaction mixture was stirred for 16 hours at room temperature, filtered over dicalite and evaporated to dryness. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→50:50 gradient). The desired compound was obtained as a light yellow liquid (240 mg, 48%).

後処理

  1. filtrationfiltered over dicalite
  2. customevaporated to dryness
  3. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→50:50 gradient)

出典と根拠

ORDレコード
ord-cb0e570cbeaf4cb9b95e377c6d650161
出典データセット
uspto-grants-2012_01
特許番号
US08097637B2

反応ノート

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