Triphenylphosphine → Diethyl [4-aminobutyl][3-(3-pyridyl)propyl]-malonate

HRID 1494064Notes

Reaction equation

HRID 1494064 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 10068124Propanedioic acid, (4-azidobutyl)[3-(3-pyridinyl)propyl]-, diethyl ester

Product 1

HCID 10383244Diethyl [4-aminobutyl][3-(3-pyridyl)propyl]-malonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 42.59 g (0.11 mole) of diethyl [4-azidobutyl][3-(3-pyridyl)-propyl]-malonate in 270 mL THF and 3.1 mL water is added 29 g (0.11 mole) of triphenyl phosphine and the solution is stirred well for 48 hours. Solvent is evaporated and the residue subjected to flash chromatography to give diethyl [4-aminobutyl][3-(3-pyridyl)- propyl]malonate as an oil.

Workup

  1. customSolvent is evaporated

Sources & evidence

ORD record
ord-a882fe55e14941d6a47d6dc0a71b9516
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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