Sodium Hydroxide → 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

HRID 2228275ノート

反応式

HRID 2228275 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:27]4[CH2:26][CH2:25][CH2:24][C:23]([C:28]([O:30]C)=[O:29])=[CH:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH:14]([C:17]3[C:27]4[CH2:26][CH2:25][CH2:24][C:23]([C:28]([OH:30])=[O:29])=[CH:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 18472663methyl 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

生成物 1

HCID 184723754-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid収率 58.4%

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

To a solution of methyl 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (1.0 g) in ethanol/THF (20/40 ml) was added at room temperature 1N sodium hydroxide solution (2.7 ml), and the mixture was stirred for 13 hours. Under reduced pressure, the mixture was concentrated. To the mixture was added water, and the mixture was washed with ethyl acetate. To the aqueous layer was added 1N hydrochloric acid (5 ml), and the mixture was extracted with ethyl acetate/THF. The organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the resulting colorless crystals were collected by filtration, which were washed with hexane to give colorless crystals of 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (565.4 mg).

後処理

  1. concentrationUnder reduced pressure, the mixture was concentrated
  2. additionTo the mixture was added water
  3. washthe mixture was washed with ethyl acetate
  4. additionTo the aqueous layer was added 1N hydrochloric acid (5 ml)
  5. extractionthe mixture was extracted with ethyl acetate/THF
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationUnder reduced pressure, the mixture was concentrated
  9. filtrationthe resulting colorless crystals were collected by filtration, which
  10. washwere washed with hexane

出典と根拠

ORDレコード
ord-1de346c2c9a7498a884f69518e03795f
出典データセット
uspto-grants-2002_07
特許番号
US06413947B1

反応ノート

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