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

HRID 394048ノート

反応式

HRID 394048 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fa934fb427fa461cb9c3ad4d8dbc1d09
出典データセット
uspto-grants-2004_10
特許番号
US06809108B1

反応ノート

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