1-(Prop-2-yn-1-yl)pyrrolidin-2-one → HCID 23509810, compound

HRID 1882876Notes

Reaction equation

HRID 1882876 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH:8]=[N:9][OH:10])[CH2:3]1.[CH2:11]([N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19])[C:12]#[CH:13]>>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:13]=[C:12]([CH2:11][N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:19])[O:10][N:9]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 124643131-(Prop-2-yn-1-yl)pyrrolidin-2-oneHCID 74057868HCID 74057868, compound

Product 1

HCID 23509810HCID 23509810, compoundYield 50.1%

Procedure

The desired compound was prepared by the method of Example 8 from 300 mg (2.11 mmol) of 1-methyl-piperidin-3-carbaldehyde oxime prepared in Example 5 and 520 mg (2 equivalents) of 1-propargyl pyrrolidin-2-one prepared in Example 7, and purified by separation with silica gel column chromatography using chloroform/methanol (gradient of 20:1 to 10:1) as eluent to obtain 278.1 mg (50% yield) of 1-[3-(1-methyl-piperidin-3-yl)-isoxazol-5-yl-methyl]-pyrrolidin-2-one. Subsequently, 1:1 acid addition salt with oxalic acid was obtained from the diethyl ether solution.

Workup

  1. custompurified by separation with silica gel column chromatography

Sources & evidence

ORD record
ord-c04eb53a53f2453c9aa71764f99516c2
Source dataset
uspto-grants-2004_07
Patent number
US06759419B2

Reaction notes

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