Potassium Cyanide → 2-(Dimethylamino)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methylpropanenitrile

HRID 20824

反応式

HRID 20824 の反応式
[Si:1]([O:8]CC(=O)C)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.CNC.[C-]#N.[K+].[CH3:20][N:21]([CH3:29])[C:22]1([C:27]#[N:28])[CH2:26]CC[CH2:23]1>O>[CH3:29][N:21]([CH3:20])[C:22]([CH3:23])([CH2:26][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:27]#[N:28]

参加物

6

反応物 4

HCID 9032Potassium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 41249691-(tert-Butyldimethylsilyloxy)-2-propanoneHCID 107730491-(Dimethylamino)cyclopentanecarbonitrile

生成物 1

HCID 866249472-(Dimethylamino)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methylpropanenitrile収率 45%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

The title compound (2.16 g, 45%) was prepared from 1-(t-butyldimethylsilyloxy)-2-propanone (3.77 g, 0.02 mol), dimethylamine hydrochloride (1.71 g, 0.02 mol) and potassium cyanide (1.37 g, 0.02 mol) in water (50 ml) in a similar manner to that described in D1. An additional purification step was passage of the compound through SCX resin, elution with DCM to remove the starting material and then elution with 1 M ammonia in methanol to elute the title compound. 1H NMR (CDCl3) δ: 0.00 (6H, d), 0.81 (9H, s), 1.38 (3H, s), 2.25 (6H, s), 3.36 (1H, d), 3.78 (1H, d).

後処理

  1. customAn additional purification step
  2. washthrough SCX resin, elution with DCM
  3. customto remove the starting material
  4. washelution with 1 M ammonia in methanol
  5. washto elute the title compound

出典と根拠

ORDレコード
ord-5fd80737275245489c89580e16169001
出典データセット
uspto-grants-2010_06
特許番号
US07745642B2

関連ノート

読み込み中…