Benzaldehyde → (S)-ethyl 1-benzyl-3-piperidinecarboxylate

HRID 432830

反応式

HRID 432830 の反応式
[NH:1]1[CH2:11][CH2:10][CH2:9][C@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([BH3-])#N.[Na+]>CO.ClCCl>[CH2:12]([N:1]1[CH2:11][CH2:10][CH2:9][C@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 240BenzaldehydeHCID 187784Ethyl (3S)-piperidine-3-carboxylateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 763479(S)-ethyl 1-benzyl-3-piperidinecarboxylate収率 39.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

(S)-ethyl nipecotate (309.1 mg; 1.97 mmol) was dissolved in anhydrous methanol (8 ml) and commercially available benzaldehyde (200 μl; 1.97 mmol) was added, followed by sodium cyanoborohydride (234 mg; 3.72 mmol). This mixture was allowed to stir at ambient temperature for 23 hours and was then diluted with dichloromethane. The dichloromethane was washed with water, then washed with saturated sodium chloride solution, dried with anhydrous potassium carbonate, and evaporated under reduced pressure at ambient temperature. The crude product was purified by chromatography on silica eluting with 50% ethyl acetate/50% hexane, giving (S)-ethyl 1-benzyl-3-piperidinecarboxylate (192.7 mg) as a colorless oil. MS mi/z (positive ion) 248 (MH+; 100).

後処理

  1. washThe dichloromethane was washed with water
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous potassium carbonate
  4. customevaporated under reduced pressure at ambient temperature
  5. customThe crude product was purified by chromatography on silica eluting with 50% ethyl acetate/50% hexane

出典と根拠

ORDレコード
ord-472ed590b85742f8a3342adc795a622e
出典データセット
uspto-grants-2003_12
特許番号
US06664271B1

関連ノート

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