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

HRID 20824Notes

Reaction equation

HRID 20824 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5fd80737275245489c89580e16169001
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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