1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile → 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile

HRID 1453051Notes

Reaction equation

HRID 1453051 reaction equation
[CH:1]1([C:6]([OH:31])([CH2:21][C:22]2[O:23][C:24]([CH3:30])([CH3:29])[O:25][C:26](=[O:28])[CH:27]=2)[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]#[N:19])[CH2:17][CH2:16]3)=[C:11]([F:20])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.[OH-].[OH-].[Pd+2]>[CH:1]1([C:6]([OH:31])([CH2:21][C:22]2[O:23][C:24]([CH3:29])([CH3:30])[O:25][C:26](=[O:28])[CH:27]=2)[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]#[N:19])[CH2:17][CH2:16]3)=[C:11]([F:20])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 587623341-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile

Product 1

HCID 587625831-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-cyclopropanecarbonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution 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}-cyclopropanecarbonitrile (1.0 g, 2.4 mmol) from Step 5 above dissolved in EtOH (20 mL) was added Pd(OH)2/C (20% wt dry basis, 100 mg) and the reaction was stirred under a hydrogen atmosphere for 6 hours. The palladium catalyst was removed by filtration, and the solvent removed by rotary evaporation. The resulting oil was used without further purification (1.02 g, 99% yield). MS (ESI): 426 (M−H).

Workup

  1. customThe palladium catalyst was removed by filtration
  2. customthe solvent removed by rotary evaporation
  3. customThe resulting oil was used without further purification (1.02 g, 99% yield)

Sources & evidence

ORD record
ord-2e74c3adb8a64447b8af852823f8c83a
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

Loading…