Sodium Azide → (S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate

HRID 394048노트

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HRID 394048 반응식
CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:20]([CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[N+:21]=[N-:22]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 10469651(S)-[[(Methylsulfonyl)oxy]methyl]piperidine-1-carboxylic Acid tert-Butyl Ester

생성물 1

HCID 10083012(S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate수율 84.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of 10.50 g of {(3S)-1-(tert-butoxycarbonyl)-3-piperidyl}methyl methanesulfonate in 100 ml of N,N-dimethylformamide, 4.9 g of sodium azide was added at room temperature, followed by 4 hours' stirring at 80° C. under heating. The reaction liquid was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and resulting residue was purified by means of silica gel column chromatography (eluting solvent: from hexane to hexane/ethyl acetate=15/1) to provide 7.24 g of the title compound.

후처리

  1. temperatureunder heating
  2. customThe reaction liquid
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customresulting residue
  7. customwas purified by means of silica gel column chromatography (eluting solvent: from hexane to hexane/ethyl acetate=15/1)

출처 및 근거

ORD 기록
ord-fa934fb427fa461cb9c3ad4d8dbc1d09
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809108B1

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