(Diethylamino)sulfur trifluoride → Tert-butyl (2-fluoro-2-methylpropyl)carbamate

HRID 81931ノート

反応式

HRID 81931 の反応式
O[C:2]([CH3:13])([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(S(F)(F)[F:20])CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:20][C:2]([CH3:13])([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

参加物

5

反応物 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 11106129tert-Butyl 2-hydroxy-2-methylpropylcarbamate

生成物 1

HCID 72698934Tert-butyl (2-fluoro-2-methylpropyl)carbamate収率 79.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

A stirred solution of tert-butyl 2-hydroxy-2-methylpropylcarbamate (7.81 g, 41.3 mmol) dissolved in 300 mL of anhydrous CH2Cl2 was cooled to −78° C. under an atmosphere of N2. The reaction mixture was treated with diethylaminosulfur trifloride (DAST) (6.2 mL, 47 mmol) and allowed to warm to ambient temperature overnight. The reaction mixture was treated with saturated NaHCO3 solution and the layers were separated. The organic portion was washed successively with saturated NaHCO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 10% EtOAc/hexanes) gave 6.27 g of tert-butyl 2-fluoro-2-methylpropylcarbamate as an amber oil which solidified on standing.

後処理

  1. temperatureto warm to ambient temperature overnight
  2. customthe layers were separated
  3. washThe organic portion was washed successively with saturated NaHCO3 solution, H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3121fa39df234ee09ca8bb9d34c239bd
出典データセット
uspto-grants-2014_09
特許番号
US08846710B2

反応ノート

読み込み中…