Diethyl Ether → Methyl 5-(4-piperidyl)pentanoate

HRID 257738노트

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HRID 257738 반응식
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:17](O)=O)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.C[CH2:21][O:22][CH2:23]C.S(Cl)(Cl)=[O:26].[N+](=C)=[N-]>N1C=CC=CC=1.CO.C([O-])(=O)C1C=CC=CC=1.[Ag+].CCN(CC)CC>[NH:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:21]([O:22][CH3:23])=[O:26])[CH2:12][CH2:13]1

참가 물질

9

반응물 4

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 24386Thionyl ChlorideHCID 104009874-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)butanoic acid

생성물 1

HCID 19781432Methyl 5-(4-piperidyl)pentanoate

시약·촉매·용매 4

HCID 1049Pyridine촉매HCID 164649Silver benzoate촉매HCID 887Methanol용매HCID 8471Triethylamine용매

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온도
0 °C

실험 절차

To a stirred solution of carboxylic acid 14 (600 mg, 2.2 mmol), ether (4.0 mL), and pyridine (2 drops) at ambient temperature was added thionyl chloride in one portion to effect an exotherm. After 25 minutes the ether, pyridine, and thionyl chloride were evaporated. The intermediate acid chloride was dissolved in ether (5 mL), cooled to 0° C., then treated with an ethereal solution of diazomethane (15 mL, ~10 mmol). After 2.0 hours the excess diazomethane was removed by purging with argon. Evaporation in situ gave a solid that was dissolved in CH3OH (10 mL) then treated sequentially with NEt3 (0.5 mL) and silver benzoate (20 mg). After 15 minutes the black reaction mixture was concentrated and the residue subjected to flash chromatography (silica, 10% ethyl acetate/hexanes) to give 15 (300 mg) as an oil.

후처리

  1. customAfter 25 minutes the ether, pyridine, and thionyl chloride were evaporated
  2. dissolutionThe intermediate acid chloride was dissolved in ether (5 mL)
  3. customAfter 2.0 hours the excess diazomethane was removed
  4. customby purging with argon
  5. customEvaporation in situ
  6. customgave a solid
  7. concentrationAfter 15 minutes the black reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-30a5365b4045493d9954ed939f26fbab
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264420

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