Water → HCID 86630052、化合物

HRID 2249675ノート

反応式

HRID 2249675 の反応式
CON(C)[C:4]([C@@H:6]1[CH2:10][C@@H:9]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH2:8][N:7]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[CH:4]([C@@H:6]1[CH2:10][C@@H:9]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH2:8][N:7]1[C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])=[O:5]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 86630051benzyl (2S,4R)-2-{[methoxy(methyl)amino]carbonyl}-4-(tetrahydro-2H-pyran-2-yloxy)-1-pyrrolidine-carboxylate

生成物 1

HCID 86630052HCID 86630052、化合物収率 44.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

In 33 ml of tetrahydrofuran is dissolved 3.3 g of benzyl (2S,4R)-2-{[methoxy(methyl)amino]carbonyl}-4-(tetrahydro-2H-pyran-2-yloxy)-1-pyrrolidine-carboxylate. After adding 0.64 g of lithium aluminum hydride at −70° C., the mixture thus obtained is stirred at −70° C. for one hour. After dropwise adding 33 ml of ethyl acetate to the reaction mixture over a period of 30 minutes and then 66 ml of tetrahydrofuran containing 20% of water over a period of 30 minutes, the mixture thus obtained is stirred at ambient temperature for 30 minutes. The mixture is filtered with Celite, and the organic layer is separated from the filtrate. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1) to obtain 1.25 g of benzyl (2S,4R)-2-formyl-4-(tetrahydro-2H-pyran-2-yloxy)-1-pyrrolidinecarboxylate as a light yellow oily product.

後処理

  1. customthe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringis stirred at ambient temperature for 30 minutes
  4. filtrationThe mixture is filtered with Celite
  5. customthe organic layer is separated from the filtrate
  6. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. customThe residue thus obtained
  10. customis purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-c1ded361337b4b5c90dfeb7554dab928
出典データセット
uspto-grants-2008_01
特許番号
US07314888B1

反応ノート

読み込み中…