Pyrrolidine → HCID 15157468, compound

HRID 2371643Notes

Reaction equation

HRID 2371643 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].N1[CH2:19][CH2:18][CH2:17][CH2:16]1>C1(C)C=CC=CC=1>[CH2:16]([C:5]1([CH2:4][CH2:3][CH:2]=[CH2:1])[CH2:13][C:11](=[O:12])[C:8]2[CH:7]=[CH:6][C:5]([OH:14])=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=2[O:10]1)[CH2:17][CH:18]=[CH2:19]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 15157468HCID 15157468, compoundYield 208.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 719 mg (5.21 mmol) of the title product of Example 63, 970 mg (5.00 mmol) of 2,4-dihydroxy-3-propylacetophenone, 360 mg (5.00 mmol) of pyrrolidine, and 5.5 ml of toluene containing 2.0 g of 3A molecular sieves was stirred at reflux for six hours, then kept overnight at room temperature. The solution was then decanted from the sieves, and the sieves were washed with methylene chloride. The solvent was then removed under reduced pressure. Chromatography of the residue over silica gel, using 14:5:1 methylene chloride:hexane:ethylacetate as eluent, gave the title compound (439 mg) as a solid.

Sources & evidence

ORD record
ord-f50cfca2ce984bd1a4cac3cc700b5552
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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