Acetic Acid → Methyl 4-{1-[2-(4-cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethoxy}benzoate

HRID 967772ノート

反応式

HRID 967772 の反応式
C(O)(=O)C.[CH3:5][O:6][C:7]([C:9]1[CH:23]=[CH:22][C:12]([O:13][CH2:14][C:15]2([OH:21])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)=[O:8].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH:33]=O)=[CH:28][CH:27]=1)#[N:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:24]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][N:18]2[CH2:17][CH2:16][C:15]([CH2:14][O:13][C:12]3[CH:11]=[CH:10][C:9]([C:7]([O:6][CH3:5])=[O:8])=[CH:23][CH:22]=3)([OH:21])[CH2:20][CH2:19]2)=[CH:28][CH:27]=1)#[N:25]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 125916704-(2-Oxoethyl)benzonitrileHCID 222912904-(4-Methoxycarbonylphenoxymethyl)piperidin-4-ol

生成物 1

HCID 10157471Methyl 4-{1-[2-(4-cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethoxy}benzoate収率 39.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Acetic acid (11.5 mL) was added to a dichloromethane solution (450 mL) of the compound (17.7 g) obtained in Step 6 and the compound (19.4 g) obtained in Step 1 of Example 1 at room temperature and the mixture was stirred at the same temperature for thirty minutes. Sodium triacetoxyborohydride (56.6 g) was added to the mixture under cooling with ice-water and the mixture was stirred at the same temperature for thirty minutes and further stirred at room temperature for five hours. The solvent was removed under reduced pressure and insoluble matter (16.1 g) precipitated by adding water (250 mL) and ethyl acetate (250 mL) was collected by filtration. To the obtained insoluble matter (13.0 g) was added water (50 mL) and saturated aqueous sodium hydrogencarbonate solution (150 mL) and the residue was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue was crystallized from ether-hexane to obtain the titled compound (10.3 g) as crystals. The physical data of the obtained compound accord with those of the compound of Example 3.

後処理

  1. stirringfurther stirred at room temperature for five hours
  2. customThe solvent was removed under reduced pressure and insoluble matter (16.1 g)
  3. customprecipitated
  4. additionby adding water (250 mL) and ethyl acetate (250 mL)
  5. filtrationwas collected by filtration
  6. additionTo the obtained insoluble matter (13.0 g) was added water (50 mL) and saturated aqueous sodium hydrogencarbonate solution (150 mL)
  7. extractionthe residue was extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe obtained residue was crystallized from ether-hexane

出典と根拠

ORDレコード
ord-684a317dfebc48198fb9a5d11b4bb92a
出典データセット
uspto-grants-2005_10
特許番号
US06956046B2

反応ノート

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