Ethyl 2-cyano-3-phenylpropanoate → Ethyl 3-amino-2-benzylpropanoate

HRID 727485

Reaction equation

HRID 727485 reaction equation
[CH2:1]([CH:8]([C:14]#[N:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[Ni]>[NH2:15][CH2:14][CH:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 1

HCID 228103Ethyl 2-cyano-3-phenylpropanoate

Product 1

HCID 19611763Ethyl 3-amino-2-benzylpropanoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The resulting ethyl benzylcyanoacetate was dissolved in 200 ml of EtOH and hydrogenated over Raney nickel. After removal of the catalyst by filtration with suction and concentration, 8.2 . . . of oil were obtained, and chromatography over silica gel (EA to EA/MeOH 5/1) gave 5.5 g of ethyl 3-amino-2-benzylpropionate. This compound was reacted with Boc2O to give ethyl 2-benzyl-3-(tert.-butoxycarbonylamino)-propionate, which was hydrolyzed, and the product was coupled with H-Val-OMe by the PPA method. The resulting diastereomers were resolved by chromatography (toluene/diisopropyl ether 1/1).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationwith suction and concentration, 8.2
  4. customof oil were obtained

Sources & evidence

ORD record
ord-90bd783a37ef46e9a04450fc5a2839c3
Source dataset
uspto-grants-1998_01
Patent number
US05712417

Linked notes

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