1,2,3,6-Tetrahydropyridine → tert-Butyl 4-(5,6-dihydropyridin-1(2H)-yl)piperidine-1-carboxylate

HRID 501957

반응식

HRID 501957 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:15]1[CH2:20][CH:19]=[CH:18][CH2:17][CH2:16]1.C([BH3-])#N.[Na+]>[Cl-].[Zn+2].[Cl-].CO>[N:15]1([CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH2:20][CH2:19][CH:18]=[CH:17][CH2:16]1

참가 물질

6

반응물 3

HCID 127501,2,3,6-TetrahydropyridineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 59424368tert-Butyl 4-(5,6-dihydropyridin-1(2H)-yl)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매

실험 절차

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (797 mg, 4 mmol), 1,2,3,6-tetrahydropyridine (349 mg, 4.2 mmol), sodium cyanoborohydride (126 mg, 2 mmol), zinc chloride (410 mg, 3.2 mmol), and anhydrous methanol (20 mL) were mixed together and the mixture stirred overnight at room temperature. The solvent was evaporated from the mixture and the residue partitioned between 1 N sodium hydroxide and dichloromethane. The phases were separated and the aqueous layer extracted with dichloromethane. The organic extracts were combined, dried over magnesium sulfate, and the solvent evaporated. The residue was purified by flash column chromatography (1:1 hexanes/ethyl acetate to ethyl acetate to 1:3 methanol/ethyl acetate) to give 800 mg (75%) as a colorless oil. 1H-NMR (CDCl3, 400 MHz) δ 5.75-5.70 (m, 1H), 5.68-5.64 (m, 1H), 4.13-4.07 (m, 2H), 3.08 (m, 2H), 2.71-2.60 (m, 4H), 2.48-2.41 (m, 1H), 2.15 (m, 2H), 1.82-1.79 (m, 2H), 1.49-1.38 (m, 11H).

후처리

  1. customThe solvent was evaporated from the mixture
  2. customthe residue partitioned between 1 N sodium hydroxide and dichloromethane
  3. customThe phases were separated
  4. extractionthe aqueous layer extracted with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated
  7. customThe residue was purified by flash column chromatography (1:1 hexanes/ethyl acetate to ethyl acetate to 1:3 methanol/ethyl acetate)
  8. customto give 800 mg (75%) as a colorless oil

출처 및 근거

ORD 기록
ord-38ba99de91ff427386a7fe8cf8cd7404
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772244B2

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