HCID 12764929, compound → HCID 14003418, compound

HRID 569750Notes

Reaction equation

HRID 569750 reaction equation
[C:1]([CH:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:2]>[Ni].C(O)C>[NH2:2][CH2:1][CH:3]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 12764929HCID 12764929, compound

Product 1

HCID 14003418HCID 14003418, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

About 10 ml of Raney nickel were added to a solution of 58 g of ethyl 5-cyano-5-phenylvalerate [prepared as described in step (a) above] in 400 ml of ethanol, and the mixture was stirred for 2.5 hours at 40° C., under a hydrogen pressure of 3 kg/cm2. The catalyst was filtered off and the filtrate was condensed to give ethyl 6-amino-5-phenylhexanoate as an oily substance. The whole of this oily substance was dissolved in 300 ml of methylene chloride, and 40 ml of triethylamine were added to the mixture. 55 g of di-t-buty pyrocarbonate were added to this solution in an ice-bath. The mixture was stirred for 1 hour, and then the solvent was evaporated off under reduced pressure. The residue was dissolved in ethyl acetate and water. The ethyl acetate layer was separated and washed with an aqueous solution of potassium bicarbonate and then with an aqueous solution of sodium chloride. It was then dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residual syrup was mixed with cyclohexane and allowed to stand. The crystals which separated out were collected by filtration as the title product, yield 25 g. The filtrate was condensed and subjected to silica gel column chromatography using a 1:5 by volume mixture of ethyl acetate and cyclohexane as eluent, to give a further 20.5 g of the title compound as crystals, melting at 82°-84° C. Total yield 45.5 g.

Workup

  1. filtrationThe catalyst was filtered off
  2. customcondensed

Sources & evidence

ORD record
ord-9b454f7c0e0f4463928f31b6cdd5ee0c
Source dataset
uspto-grants-1988_03
Patent number
US04734410

Reaction notes

Loading…