1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile → 2-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-propionitrile

HRID 858694Notes

Reaction equation

HRID 858694 reaction equation
[CH:1]1([C:6]([OH:30])([CH2:20][C:21]2[O:22]C(C)(C)[O:24][C:25](=O)[CH:26]=2)[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:18])[C:16]#[N:17])=[C:11]([F:19])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(O)(CC2OC(C)(C)OC(=O)C=2)C#CC2C=CC(C3(C#N)CCC3)=C(F)C=2)CCCC1>>[CH:1]1([C:6]2([CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([CH:15]([CH3:18])[C:16]#[N:17])=[C:11]([F:19])[CH:10]=3)[CH2:20][C:21](=[O:22])[CH2:26][C:25](=[O:24])[O:30]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 587622991-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclobutanecarbonitrileHCID 587625582-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-propionitrile

Product 1

HCID 587622802-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-propionitrile

Procedure

The title compound was prepared analogously to example A(237) substituting 2{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-propionitrile from step 2 below in place of 1-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile. 1H NMR (400 MHz, CDCl3) δ: 1.33–1.50 (m, 3H), 1.56 (d, J=7.33 Hz, 3H), 1.62–1.75 (m, 5H), 1.85–1.93 (m, 2H), 2.15–2.26 (m, 1H), 2.58–2.68 (m, 3H), 2.72 (d, J=6.57 Hz, 2H), 3.38 (d, J=3.54 Hz, 2H), 4.09 (q, J=7.33 Hz, 1H), 6.84 (d, J=11.12 Hz, 1H), 6.93 (d, J=7.83 Hz, 1H), 7.34 (t, J=7.83 Hz, 1H).

Sources & evidence

ORD record
ord-ac5568dc20ae478a8a832693b365df14
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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