Methyl Nicotinate → Myosmine

HRID 384844

反応式

HRID 384844 の反応式
C([N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=O)=CCC.C(OC)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1>CN(C=O)C>[CH:16]1[CH:15]=[N:14][CH:13]=[C:12]([C:6]2[CH2:7][CH2:8][CH2:9][N:5]=2)[CH:17]=1

参加物

4

反応物 2

HCID 7151Methyl NicotinateHCID 5801701-(But-1-enyl)pyrrolidin-2-one

生成物 1

HCID 442649Myosmine収率 77.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Sodium hydride (17.26 g, 072 mol of 60% dispersion in a mineral oil) was washed with toluene (25 ml×2) to remove mineral oil and added to 25 ml of DMF. To this a solution containing 1-(but-1-enyl)-pyrrolidin-2-one (I, 50 g, 0.3597 mol) and methyl nicotinate (41.8 g, 0.3057 mol) in 50 ml of DMF was added. The reaction mixture was heated to 90° C. for 2 hrs. DMF was partially removed under reduced pressure and 100 ml water and HCl (165 ml) were added. The reaction mixture was heated to 110° C. for 12 hr, cooled and washed with ethyl acetate (50 ml×2). The aqueous layer was cooled to 0° C., pH adjusted to about 14 using NaOH, extracted with dichloromethane (100 ml×4), the extract dried over Na2SO4, the solvent removed completely and the crude solid was purified by high vacuum distillation to get myosmine (34.38 g, 77.2% yield, 98.5% purity by GC).

後処理

  1. washSodium hydride (17.26 g, 072 mol of 60% dispersion in a mineral oil) was washed with toluene (25 ml×2)
  2. customto remove mineral oil
  3. additionadded to 25 ml of DMF
  4. additionwas added
  5. customDMF was partially removed under reduced pressure and 100 ml water and HCl (165 ml)
  6. additionwere added
  7. temperatureThe reaction mixture was heated to 110° C. for 12 hr
  8. temperaturecooled
  9. washwashed with ethyl acetate (50 ml×2)
  10. temperatureThe aqueous layer was cooled to 0° C.
  11. extractionextracted with dichloromethane (100 ml×4)
  12. dry with materialthe extract dried over Na2SO4
  13. customthe solvent removed completely
  14. distillationthe crude solid was purified by high vacuum distillation

出典と根拠

ORDレコード
ord-33517937e2044864ac997c57c365dae4
出典データセット
uspto-grants-2013_02
特許番号
US08367837B2

関連ノート

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