Ammonium Chloride → Rac-1-azido-4-(tert-butyl-dimethyl-silanyloxy)-butan-2-ol

HRID 1916324ノート

反応式

HRID 1916324 の反応式
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]1[CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].[N-:14]=[N+:15]=[N-:16].[Na+].[NH4+].[Cl-]>CO>[N:14]([CH2:11][CH:9]([OH:10])[CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:13])[CH3:12])=[N+:15]=[N-:16]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 11030897(R)-tert-butyldimethyl(2-(oxiran-2-yl)ethoxy)silane

生成物 1

HCID 91149373Rac-1-azido-4-(tert-butyl-dimethyl-silanyloxy)-butan-2-ol収率 81%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-[2-[[(tert-butyl)dimethylsilyl]oxy]ethyl]-oxirane (5.0 g; prepared according to WO 2007/144423) in MeOH (150 mL) was reacted with NaN3 (3.95 g) and NH4Cl (2.37 g). The reaction mixture was further stirred at 80° C. overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between EA and water. The org. layer was washed with brine, dried over Na2SO4 and evaporated under reduced pressure, affording a yellow oil (4.9 g; 81% yield).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between EA and water
  3. washlayer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customaffording a yellow oil (4.9 g; 81% yield)

出典と根拠

ORDレコード
ord-333cec5958144505a623eb4ab2d6f229
出典データセット
uspto-grants-2013_12
特許番号
US08618092B2

反応ノート

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