Trimethylsilyl cyanide → 2-Amino-1-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)ethan-1-ol

HRID 1033017Notes

Reaction equation

HRID 1033017 reaction equation
[CH3:1][O:2][C:3]1[N:10]=[C:9]([CH3:11])[C:8]([CH2:12][CH3:13])=[CH:7][C:4]=1[CH:5]=[O:6].C[Si]([C:18]#[N:19])(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.[I-].[Zn+2].[I-]>[CH3:1][O:2][C:3]1[C:4]([CH:5]([OH:6])[CH2:18][NH2:19])=[CH:7][C:8]([CH2:12][CH3:13])=[C:9]([CH3:11])[N:10]=1

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 102616792-Methoxy-5-ethyl-6-methylnicotinaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 103307592-Amino-1-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 2-methoxy-5-ethyl-6-methylnicotinaldehyde (1.05 g, 5.86 mmol) and trimethylsilyl cyanide (0.85 mL, 6.37 mmol) containing zinc iodide (10 mg) was stirred, under a nitrogen atmosphere, at ambient temperature for two hours. This liquid was diluted with anhydrous diethyl ether, filtered and then added dropwise to a suspension of lithium aluminum hydride (225 mg, 5.9 mmol) in diethyl ether (15 mL) under nitrogen. After two hours the reaction was quenched with saturated aqueous sodium sulfate, diluted with methylene chloride, filtered and the solvents evaporated to give a semi-solid. This residue was triturated with cold diethyl ether and the crystalline product was collected by filtration to yield 346 mg (28%).

Workup

  1. filtrationfiltered
  2. customAfter two hours the reaction was quenched with saturated aqueous sodium sulfate
  3. additiondiluted with methylene chloride
  4. filtrationfiltered
  5. customthe solvents evaporated
  6. customto give a semi-solid
  7. customThis residue was triturated with cold diethyl ether
  8. filtrationthe crystalline product was collected by filtration
  9. customto yield 346 mg (28%)

Sources & evidence

ORD record
ord-989f814f22c349e0b0631f4de664ba38
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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