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

HRID 1453058Notes

Reaction equation

HRID 1453058 reaction equation
[CH:1]1(C(O)(CC2OC(C)(C)OC(=O)C=2)CCC2C=CC(C(CC)(CC)C#N)=C(F)C=2)CCC[CH2:2]1.[CH:34]1([C:39]([OH:64])([CH2:54][C:55]2[O:56]C(C)(C)O[C:59](=[O:61])[CH:60]=2)[CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]3([C:51]#[N:52])[CH2:50][CH2:49]3)=[C:44]([F:53])[CH:43]=2)[CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH:34]1([C:39]2([CH2:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([C:48]([CH2:1][CH3:2])([CH2:50][CH3:49])[C:51]#[N:52])=[C:44]([F:53])[CH:43]=3)[CH2:54][C:55](=[O:56])[CH2:60][C:59](=[O:61])[O:64]2)[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 587625831-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-cyclopropanecarbonitrileHCID 587626112-(4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-2-ethyl-butyronitrile

Product 1

HCID 252323432-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl)-2-ethyl-butyronitrile

Procedure

The desired product was prepared analogously to Example A(86) step 5, substituting 2-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-2-ethyl-butyronitrile (0.84 g, 1.8 mmol) from step 3 below in place of 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile. Yield: 0.393 g, 54%. 1H NMR (CDCl3) δ: 1.01 (t, J=7.45 Hz, 6H), 1.62-1.90 (br, 8H), 2.03-2.17 (br, 4H), 2.20-2.29 (br, 2H), 2.37 (p, J=9.35 Hz, 1H), 2.75-2.82 (m, 2H), 2.86 (d, J=7.58 Hz, 2H), 3.53 (d, J=2.02 Hz, 2H), 6.94 (dd, J1 =13.01 Hz, J2=1.64 Hz, 1H), 7.04 (dd, J1=7.83 Hz, J2=1.77 Hz, 1H), 7.57 (t, J=8.21 Hz, 1H).

Sources & evidence

ORD record
ord-c9982c622ba947e5889bed234eb4413d
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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