tert-butyl N-(4-cyano-2-vinylbenzyl)-N-methylglycinate → tert-butyl N-(4-cyano-2-ethylbenzyl)-N-methylglycinate

HRID 2404348Notes

Reaction equation

HRID 2404348 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:5]([CH:20]=[CH2:21])[CH:4]=1)#[N:2]>[Pd].CO>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[C:5]([CH2:20][CH3:21])[CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 66678475tert-butyl N-(4-cyano-2-vinylbenzyl)-N-methylglycinate

Product 1

HCID 66678155tert-butyl N-(4-cyano-2-ethylbenzyl)-N-methylglycinateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl N-(4-cyano-2-vinylbenzyl)-N-methylglycinate (500 mg, 1.75 mmol) and 10% palladium on carbon (50 mg) in methanol (5 mL) were stirred under an atmosphere of hydrogen for 18 hours. The suspension was filtered through a Celite pad and the filter-cake washed with DCM. The filtrate was evaporated in vacuo to afford the title compound (474 mg, 94%).

Workup

  1. filtrationThe suspension was filtered through a Celite pad
  2. washthe filter-cake washed with DCM
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c97375573f0647c09bc0f0b46a58e92f
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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