Methylamine → HCID 20077140, compound

HRID 1655106Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]=O)[O:4][N:3]=1.[CH3:9][NH2:10].[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12]1>>[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]2[CH:13]([C:14]([OH:16])=[O:15])[CH2:12][C:11](=[O:17])[N:10]2[CH3:9])[O:4][N:3]=1

Participants

Reactant 3

HCID 6329Methylamine

HCID 7922Succinic anhydride

HCID 105827583-Methyl-1,2-oxazole-5-carbaldehyde

Product 1

HCID 20077140HCID 20077140, compound

Procedure

3-Methyl-5-formyl-isoxazole (prepared following the procedure of Tetrahedron Lett., (32), 2961-4, 1979) is reacted with methylamine and succinic anhydride to provide 3-methyl-5-(1-methyl-3-carboxy-5-oxo-2-pyrrolidinyl)-isoxazole. This acid is converted to the ester and then selectively reduced with sodium borohydride to give the corresponding alcohol, which is reacted with methanesulfonyl chloride. The resulting mesylate is converted to the fluoromethyl isoxazole by treatment with tetrabutylammonium fluoride. Following the procedure of Example 24b, the 3-methyl-5-(1-methyl-3-fluoromethyl-5-oxo-2-pyrrolidinyl)-isoxazole is reacted with borane, and the resulting product is converted to the oxalate salt to afford the title compound.

Sources & evidence

ORD record: ord-b0091ea08d5144188609def93d528090
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05409946

Reaction notes

Loading…