HCID 22004936, compound → HCID 22005106, compound

HRID 324889Notes

Reaction equation

HRID 324889 reaction equation
[CH:1]([C:4]1[C:5]([CH2:22][OH:23])=[C:6]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([CH:13]=[CH2:14])=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([C:4]1[C:5]([CH2:22][OH:23])=[C:6]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:7]([CH2:13][CH3:14])=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22004936HCID 22004936, compound

Product 1

HCID 22005106HCID 22005106, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The intermediate obtained in Step G (7.7 g, 24.7 mmol) was dissolved in absolute ethanol (200 mL) under argon, treated with 10% palladium on carbon (610 mg, 0.1 eq), then stirred under a hydrogen atmosphere for 2 hr. After purging the system with argon, the catalyst was removed by filtration through a pad of Celite. The solvent was removed and the product dried in vacuo to afford the title compound as a white solid (7.7 g, 25 mmol, 99%). 1H NMR (300 MHz, CDCl3): δ 7.32 (s, 1H), 7.15 (m, 4H), 4.33 (m, 2H), 3.39 (septet, J=7 Hz, 1H), 3.32 (septet, J=7 Hz, 1H), 2.37 (q, J=7.7 Hz, 2H), 1.29 (m, 13H), 0.92 (t, J=7.7 Hz, 3H). FAB-MS calculated for (C21H27FO) 314, found 314 (M+). mp 106-108° C. Rf=0.1 (50% dichloromethane/hexane).

Workup

  1. customAfter purging the system with argon
  2. customthe catalyst was removed by filtration through a pad of Celite
  3. customThe solvent was removed
  4. customthe product dried in vacuo

Sources & evidence

ORD record
ord-19a4a610f5344897b6e484e37e690adf
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

Loading…