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

HRID 598045ノート

反応式

HRID 598045 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+]>ClCCl>[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 70.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl 2-hydroxy-2-methylpropylcarbamate (19.2 g, 101 mmol) in dichloromethane (500 mL) was stirred at −78° C. under a nitrogen atmosphere, and (diethylamino)sulfur trifluoride (DAST)(18.0 g, 112 mmol) was added dropwise. The solution was allowed to warm to room temperature and stirred overnight. Saturated aqueous sodium bicarbonate (150 mL) was added. The organic layer was then separated and washed sequentially with saturated aqueous sodium bicarbonate (150 mL), water (150 mL), and brine (150 mL); dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The resulting oil was purified by automated flash chromatography (FLASH 65I cartridge, eluting with 10% ethyl acetate in hexane) to provide 13.7 g of tert-butyl 2-fluoro-2-methylpropylcarbamate as a light yellow oil that crystallized overnight.

後処理

  1. customThe organic layer was then separated
  2. washwashed sequentially with saturated aqueous sodium bicarbonate (150 mL), water (150 mL), and brine (150 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationand concentrated under reduced pressure
  6. customThe resulting oil was purified by automated flash chromatography (FLASH 65I cartridge, eluting with 10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-7e5ba8712eef419ab41071692cf4dab3
出典データセット
uspto-grants-2011_03
特許番号
US07897609B2

反応ノート

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