Sodium Hydroxide → cis-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydro spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxide

HRID 496170

反応式

HRID 496170 の反応式
[OH:1][C@@H:2]1[C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7][S:6](=[O:15])(=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[C@H:3]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>C(Cl)Cl.CCCCCCCC(C([NH3+])(C(CCCCCCC)=O)C(CCCCCCC)=O)=O.[Cl-]>[OH:1][C@@H:2]1[C:8]2([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:7][S:6](=[O:15])(=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[C@@H:3]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 59890377trans-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydo spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxide

生成物 1

HCID 59890389cis-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydro spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxide収率 62.6%

試薬・触媒・溶媒 2

HCID 77620884Tricaprylylmethyl ammonium chloride触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.2 g (0.56 mmole) of 59 in 20 ml of CH2Cl2, was added 8 g of 50% NaOH and one drop of Aliquat-336 (methyltricaprylylammonium chloride) phase transfer catalyst. The reaction mixture was stirred for 10 h at room temperature. Twenty g of ice was added to the mixture and the mixture was extracted with CH2Cl2 (3×10 ml) washed with water, brine and dried over MgSO4 and concentrated in vacuo to recover 0.15 g of crude product. This was recrystallized from Hexane/EtOAc to give 125 mg of white crystal, mp 209-210° C. Proton and carbon NMR and mass spectra were consistent with the product.

後処理

  1. additionTwenty g of ice was added to the mixture
  2. extractionthe mixture was extracted with CH2Cl2 (3×10 ml)
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto recover 0.15 g of crude product
  7. customThis was recrystallized from Hexane/EtOAc

出典と根拠

ORDレコード
ord-c8c9dd633000486b9fe5b5b33b31fd5b
出典データセット
uspto-grants-2005_09
特許番号
US06943189B2

関連ノート

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