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

HRID 420766노트

반응식

HRID 420766 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 566095Methyl 2-(3-oxocyclohexyl)acetate

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-cb0e570cbeaf4cb9b95e377c6d650161
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097637B2

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