Allyl bromide → 1-tert-Butyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate

HRID 1442902노트

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HRID 1442902 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[CH2:28](Br)[CH:29]=[CH2:30]>C1COCC1>[CH2:30]([C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]1)[CH:29]=[CH2:28]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 3251421Potassium bis(trimethylsilyl)amide

생성물 1

HCID 529878041-tert-Butyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate수율 90.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a −78° C. solution of N-Boc-4-piperidinecarboxylic acid methyl ester (5.70 g, 23.4 mmol) in THF (80 mL) was added potassium hexamethyldisilazide (0.5 M in toluene, 70.2 mL, 35.1 mmol). After 2 h allyl bromide (6.69 mL, 77.3 mmol) was added, the reaction stirred at this temperature for 0.5 h, then warmed to 0° C. After 3 h the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 0 to 8% methanol:dichloromethane to give the title compound (6.0 g). MS: m/z=284.2 (M+1).

후처리

  1. customAfter 3 h the reaction was quenched by the addition of saturated aqueous ammonium chloride
  2. extractionextracted with dichloromethane (3×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of 0 to 8% methanol

출처 및 근거

ORD 기록
ord-b68e3a2888eb44f28e14a22b93b3eae6
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659264B2

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