Pyrrolidine → HCID 66643555, compound

HRID 1807538Notes

Reaction equation

HRID 1807538 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Br)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 666436981254962-88-3

Product 1

HCID 66643555HCID 66643555, compoundYield 26.1%

Conditions

Temperature
180 °C

Procedure

A mixture containing 3-bromo-5-methyl-isoxazole-4-carboxylic acid ethyl ester (5.0 g, 18.8 mmol), pyrrolidine (13.37 g, 188 mmol) and BEMP (10.53 g, 37.6 mmol) was heated in the microwave at 180° C. for 10 min. The mixture was then extracted with ethyl acetate, dried over potassium sulphate, filtered and evaporated. Purification by chromatography (silica, ethyl acetate:methanol 1:9 to 3:7) afforded the title compound (1.1 g, 21%) as a yellow oil. MS: m/e=225.3 [M]+.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. dry with materialdried over potassium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by chromatography (silica, ethyl acetate:methanol 1:9 to 3:7)

Sources & evidence

ORD record
ord-96d9ebd4b59a4ce783e1be6c97a829d2
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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