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

HRID 858664Notes

Reaction equation

HRID 858664 reaction equation
[CH:1]1([C:6](O)([CH2:23][C:24]2[O:25]C(C)(C)[O:27][C:28](=[O:30])[CH:29]=2)[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:20]#[N:21])[CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:11]([F:22])[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(C(C)(C)C#N)=C(F)C=2)CCCC1>>[CH:1]1([C:6]2([CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4([C:20]#[N:21])[CH2:16][CH2:17][CH2:18][CH2:19]4)=[C:11]([F:22])[CH:10]=3)[CH2:23][C:24](=[O:25])[CH2:29][C:28](=[O:30])[O:27]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 587623121-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopentanecarbonitrileHCID 587626542-{4-[3-cyclopentyl-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-hydroxybut-1-ynyl]-2-fluorophenyl)-2-methylpropanenitrile

Product 1

HCID 587623021-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopentanecarbonitrile

Procedure

The title compound was prepared analogously to step 4 from Example A(97) where 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopentanecarbonitrile (from step 2 below) was substituted in place of 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-hydroxybut-1-ynyl]-2-fluorophenyl}-2-methylpropanenitrile. 1H NMR (CDCl3) δ: 1.18–1.74 (m, 16 H), 1.92–2.17 (m, 2 H), 2.5–2.52 (m, 1 H), 2.66–2.68 (m, 2 H), 2.77 (s, 2 H), 3.43 (s, 2 H), 6.89–6.94 (m, 2 H), 7.33–7.37 (m, 1 H). MS (ESI): 398 (M+H)+.

Sources & evidence

ORD record
ord-38e534aace864e40a85bf78b526e6bd2
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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