Triethylamine → Ecgonine

HRID 2254997Notes

Reaction equation

HRID 2254997 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C.[CH3:23][N:24]1[C@H:28]2[C@@H:29]([C:33]([OH:35])=[O:34])[C@@H:30]([OH:32])[CH2:31][C@@H:25]1[CH2:26][CH2:27]2.Cl>O1CCCC1.O(CCOC)C.CN(C)C1C=CN=CC=1>[CH3:23][N:24]1[C@H:28]2[C@@H:29]([C:33]([OH:35])=[O:34])[C@@H:30]([OH:32])[CH2:31][C@@H:25]1[CH2:26][CH2:27]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 451576305796-31-6

Product 1

HCID 91460Ecgonine

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 1.93 g (4.5 mmole) of the above compound in 20 mL of dry tetrahydrofuran and 5 mL of 1,2-dimethoxylethane was treated with 0.52 g (2.5 mmole) of 1,3-dicyclohexylcarbodiimide. This mixture was stirred and heated at 45° C. for 72 hours. Then, triethylamine (0.6 mL), 4-dimethylaminopyridine (250 mg) and ecgonine hydrochloride (0.55 g, 2.4 mmole) were added, and the reaction was concentrated in vacuo to a dark, semi-solid residue which was taken up in a minimum of dichloromethane and applied atop a column packed with 60.0 g of Merck "60" silica gel. The column was eluted with a gradient of 20 to 40% of methanol in ethyl acetate. The homogeneous fractions showed an Rf on silica gel plates of 0.16 in 3:1 methanol/acetate containing 1% of NH4OH solution. There was obtained 230 mg of [4-(6-carbobenzyloxy-aminocaproyl) aminobenzoyl] ecgonine as an amorphous powder.

Workup

  1. concentrationthe reaction was concentrated in vacuo to a dark, semi-solid residue which
  2. washThe column was eluted with a gradient of 20 to 40% of methanol in ethyl acetate

Sources & evidence

ORD record
ord-1e6946cfdbb345358ee75acf2f7f9dab
Source dataset
uspto-grants-1993_08
Patent number
US05238652

Reaction notes

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