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

HRID 20824

반응식

HRID 20824 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5fd80737275245489c89580e16169001
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745642B2

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