5-Methyl-1,2-oxazole-3-carbaldehyde → 6-Cyclopentyl-6-[2-(3-fluoro 4-isopropoxy-phenyl)-ethyl]-4-hydroxy-3-(5-methyl-isoxazol-3-ylmethyl)-5,6-dihydro-pyran-2-one

HRID 858717Notes

Reaction equation

HRID 858717 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([F:26])[CH:17]=3)[O:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][C:28]1[O:32][N:31]=[C:30]([CH:33]=O)[CH:29]=1.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[C:18]([F:26])[CH:17]=3)[O:11][C:10](=[O:12])[C:9]([CH2:33][C:30]3[CH:29]=[C:28]([CH3:27])[O:32][N:31]=3)=[C:8]([OH:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 27952225-Methyl-1,2-oxazole-3-carbaldehydeHCID 6451240Aluminum(III) ChlorideHCID 160761116-(3-fluoro-4-isopropoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Product 1

HCID 587627456-Cyclopentyl-6-[2-(3-fluoro 4-isopropoxy-phenyl)-ethyl]-4-hydroxy-3-(5-methyl-isoxazol-3-ylmethyl)-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared by coupling 6-Cyclopentyl-6-[2-(3-fluoro-4-isopropoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione from Step 1 of Example B(14), to 5-Methyl-isoxazole-3-carbaldehyde using the AlCl3/reduction procedure described for Example B(13).

Sources & evidence

ORD record
ord-86ba857c31074ed49c4a227b7c303c47
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

Loading…