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

HRID 432830

반응식

HRID 432830 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-472ed590b85742f8a3342adc795a622e
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664271B1

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