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

HRID 257738

反応式

HRID 257738 の反応式
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

参加物

9

反応物 4

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

生成物 1

HCID 19781432Methyl 5-(4-piperidyl)pentanoate

試薬・触媒・溶媒 4

HCID 1049Pyridine触媒HCID 164649Silver benzoate触媒HCID 887Methanol溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-30a5365b4045493d9954ed939f26fbab
出典データセット
uspto-grants-1993_11
特許番号
US05264420

関連ノート

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