Water → tert-Butyl 3-ethyl-4-oxopiperidine-1-carboxylate

HRID 457097노트

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HRID 457097 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CC[CH2:17][CH2:16]1.O.ICC>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[CH:12]([CH2:16][CH3:17])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 962WaterHCID 6340IodoethaneHCID 31268PyrrolidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

생성물 1

HCID 22278903tert-Butyl 3-ethyl-4-oxopiperidine-1-carboxylate

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 241Benzene용매

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온도
100 °C

실험 절차

A solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (5 g, 25.1 mmol), pyrollidine (5 mL) and p-toluenesulfonic acid (25 mg) in benzene (100 mL) was heated at reflux for 16 h with azeotropic distillation of water. The resulting enamine solution was cooled to rt and concentrated. The crude enamine was dissolved in acetonitrile (50 mL); iodoethane (4.67 g, 30.1 mmol.) was added and the mixture was heated at 100° C. for 0.5 h, cooled to rt and concentrated. The mixture was dissolved in ethyl acetate (200 mL), washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine. The extract was dried over magnesium sulfate, filtered and concentrated. The crude compound was purified by silica gel chromatography (80% hexanes/20% ethyl acetate) to afford 3-ethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (680 mg).

후처리

  1. concentrationconcentrated
  2. dissolutionThe crude enamine was dissolved in acetonitrile (50 mL)
  3. temperaturecooled to rt
  4. concentrationconcentrated
  5. dissolutionThe mixture was dissolved in ethyl acetate (200 mL)
  6. washwashed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine
  7. dry with materialThe extract was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude compound was purified by silica gel chromatography (80% hexanes/20% ethyl acetate)

출처 및 근거

ORD 기록
ord-16b9aec4fa6148f191bfa3d9d1f00019
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186729B2

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