1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile → 1-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile
Reaction equation
[CH:1]1([C:6]([OH:32])([CH2:22][C:23]2[O:24]C(C)(C)O[C:27](=[O:29])[CH:28]=2)[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:19]#[N:20])[CH2:18][CH2:17][CH2:16]3)=[C:11]([F:21])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(O)(CC2OC(C)(C)OC(=O)C=2)CCC2C=CC(C3(C#N)CC3)=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:19]#[N:20])[CH2:18][CH2:17][CH2:16]4)=[C:11]([F:21])[CH:10]=3)[CH2:22][C:23](=[O:24])[CH2:28][C:27](=[O:29])[O:32]2)[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
3
Reactant 2
Product 1
Procedure
The desired product was prepared analogously to Example A(86) step 5 substituting 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-cyclobutanecarbonitrile (1.00 g, 2.2 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: 0.477 g, 57%. 1H NMR (CDCl3) δ: 1.79-2.05 (br, 8H), 2.14-2.19 (m, 2H), 2.21-2.29 (m, 1H), 2.49 (p, J=9.35 Hz, 1H), 2.65-2.76 (m 1H), 2.83-2.95 (m, 4H), 3.00 (d, J=5.05 Hz, 2H), 3.02-3.10 (m, 2H), 3.66 (d, J=3.28 Hz, 2H), 7.12 (dd, J1=11.24 Hz, J2=1.64 Hz, 1H), 7.17 (dd, J1=7.96 Hz, J2=1.64 Hz, 1H), 7.38 (t, J=7.96 Hz, 1H).
Sources & evidence
- ORD record
- ord-38b5729b91b44991b7d76b1d9592794f
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473790B2
Reaction notes
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