1-(Allyl)pyrrolidin-2-one → HCID 10106929, compound

HRID 1882875Notes

Reaction equation

HRID 1882875 reaction equation
[N:1]1([CH2:6][CH2:7][CH:8]=[N:9][OH:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:11]([N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19])[CH:12]=[CH2:13]>>[N:1]1([CH2:6][CH2:7][C:8]2[CH2:13][CH:12]([CH2:11][N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:19])[O:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 758971-(Allyl)pyrrolidin-2-oneHCID 74057869HCID 74057869, compound

Product 1

HCID 10106929HCID 10106929, compoundYield 20%

Procedure

The desired compound was prepared by the method of Example 8 from 400 mg (2.813 mmol) of 3-pyrrolidin-1-yl-propionaldehyde oxime prepared in Example 1 and 704 mg (2 equivalents) of 1-allyl pyrrolidin-2-one prepared in Example 6, and purified by separation with silica gel column chromatography using chloroform/methanol (gradient of 20:1 to 7:1) as eluent to obtain 148 mg (20% yield) of 1-[3-(2-pyrrolidin-1-yl-ethyl)-4,5-dihydro-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-b5cb135d770645678914d94db57ec2a8
Source dataset
uspto-grants-2004_07
Patent number
US06759419B2

Reaction notes

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