Diisopropylethylamine → 1-Benzyl-4-methylpiperidin-3-one

HRID 2122042ノート

反応式

HRID 2122042 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH3:25])[CH:21]([OH:26])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>ClCCl.CS(C)=O>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH3:25])[C:21](=[O:26])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 2

HCID 81531DiisopropylethylamineHCID 222535901-Benzyl-4-methylpiperidin-3-OL 4-methylbenzenesulfonate

生成物 1

HCID 120848281-Benzyl-4-methylpiperidin-3-one収率 72.97%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of the product from Method D (9.8 grams/0.026 mol) and 31.7 mL of diisopropylethylamine dissolved in 250 mL of dichloromethane and cooled to 0° C. was added (dropwise) 12.4 grams of SO3 pyridine complex dissolved in 153 mL of dimethylsulfoxide over a 40 minute period. Once added, the reaction stirred for 1.5 hours at room temperature and was then quenched upon addition of 200 mL of saturated NaHCO3 (aq). The dichloromethane was removed in vacuo and the remaining aqueous residue extracted four times with diisopropyl ether (150 mL). The combined ether layers were washed four times with water (100 mL), dried over Na2SO4 and concentrated to dryness in vacuo affording 3.81 grams (72.97%) of the title compound as yellow oil. LRMS: 204 (M+1).

後処理

  1. additionwas added (dropwise) 12.4 grams of SO3 pyridine complex
  2. additionOnce added
  3. customwas then quenched upon addition of 200 mL of saturated NaHCO3 (aq)
  4. customThe dichloromethane was removed in vacuo
  5. extractionthe remaining aqueous residue extracted four times with diisopropyl ether (150 mL)
  6. washThe combined ether layers were washed four times with water (100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-c6b46e52a69b422e9fe0e2136f9fc50f
出典データセット
uspto-grants-2004_02
特許番号
US06696567B2

反応ノート

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