m-Chloroperbenzoic acid → 5-Methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane

HRID 229784

反応式

HRID 229784 の反応式
[CH3:1][CH:2]1[CH2:8][CH:7]=[CH:6][CH2:5][N:4]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)(=[O:11])=[O:10])[CH2:3]1.C([O-])(O)=[O:19].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[CH3:1][CH:2]1[CH2:8][CH:7]2[CH:6]([O:19]2)[CH2:5][N:4]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)(=[O:11])=[O:10])[CH2:3]1

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 116302233-Methyl-1-(pyridine-2-sulfonyl)-2,3,4,7-tetrahydro-1H-azepine

生成物 1

HCID 220366865-Methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To the solution of 3-methyl-1-(pyridine-2-sulfonyl)-2,3,4,7-tetrahydro-1H-azepine (1.3 g, 5.16 mmol) in CH2Cl2 (50 ml) was added NaHCO3 (1.3 g, 15.5 mmol) and then mCPBA (2.67 g, 15.5 mmol) in portions. Stirred at RT for 4 h before worked up by washing with 15% NaOH, saturated K2CO3 and brine. Dried over Na2SO4. The reaction mixture was concentrated by rotary evaporation and two insomers were seperated on column chromatography (30%-40% EtoAc/Hexane). The first elution (trans-isomer, 230 mg) was used in next steps, the second elution (cis-insomer 200 mg) was saved: MS (M+H+): 269.0; 1H-NMR (400 Hz, CDCl3): d=8.70(d, 1H), 8.0-7.75(m, 2H), 7.50 (m, 1H) 4.39(m, 1H), 3.92(m, 1H), 3.34-2.00(m, 6H), 1.40(m, 1H), 0.88(d, 3H)

後処理

  1. washby washing with 15% NaOH, saturated K2CO3 and brine
  2. dry with materialDried over Na2SO4
  3. concentrationThe reaction mixture was concentrated by rotary evaporation and two insomers
  4. customwere seperated on column chromatography (30%-40% EtoAc/Hexane)
  5. washThe first elution (trans-isomer, 230 mg)
  6. washthe second elution (cis-insomer 200 mg)

出典と根拠

ORDレコード
ord-67f00ab6309a4916a57b51d30c8c4cdd
出典データセット
uspto-grants-2009_07
特許番号
US07563784B2

関連ノート

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