Water → tert-Butyl 4-cyano-4-methylpiperidine-1-carboxylate

HRID 390325

反応式

HRID 390325 の反応式
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[CH3:16][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC.O>C1COCC1>[C:1]([C:3]1([CH3:16])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 46835621tert-Butyl 4-cyano-4-methylpiperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 4-cyanopiperidine-1-carboxylate (0.500 g, 2.38 mmol) in 15 mL of THF at −78° C. was added lithium bis(trimethylsilyl)amide (1 M solution in diethyl ether, 5.23 mL, 5.23 mmol). After 20 min, iodomethane (0.338 g, 2.38 mmol) was added dropwise, and the reaction was slowly warmed to rt. After 15 h, the mixture was cooled to 0° C., treated with water, and extracted 3× with ethyl acetate. The solution was extracted 3× with ethyl acetate, and the combined organic solution was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide tert-butyl 4-cyano-4-methylpiperidine-1-carboxylate that gave a proton NMR spectra consistent with theory.

後処理

  1. waitAfter 15 h
  2. temperaturethe mixture was cooled to 0° C.
  3. extractionextracted 3× with ethyl acetate
  4. extractionThe solution was extracted 3× with ethyl acetate
  5. washthe combined organic solution was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-454eebe664044bada4195fc24971f482
出典データセット
uspto-grants-2013_02
特許番号
US08383638B2

関連ノート

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