1-Ethynyl-4-fluorobenzene → HCID 59066524, compound

HRID 1838002Notes

Reaction equation

HRID 1838002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[CH:10]([C@@H:12]1[N:16]([CH3:17])[C:15](=[O:18])[CH2:14][C@@H:13]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:11]>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C@H:10]([C@@H:12]2[N:16]([CH3:17])[C:15](=[O:18])[CH2:14][C@@H:13]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[OH:11])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@H:10]([C@@H:12]2[N:16]([CH3:17])[C:15](=[O:18])[CH2:14][C@@H:13]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[OH:11])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 5226271-Ethynyl-4-fluorobenzeneHCID 13825985(-)-(4R*,5R*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one

Product 2

HCID 9858383HCID 9858383, compoundHCID 59066524HCID 59066524, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

(±)-(4R*,5R*)-5-[(1R*)3-(4-Fluorophenyl) 1-hydroxyprop-2-ynyl]-1-methyl-4-phenylpyrrolidin-2-one was prepared from 4-fluorophenyl acetylene and Intermediate Z using a method analogous to that described for Examples 8. A solution of this compound (52 mg, 0.16 mmol) in EtOAc (5 mL) was added to a catalyst slurry prepared by addition of EtOAc (10 mL) to 10% Palladium on carbon (20 mg) under an Ar atmosphere. The reaction mixture was stirred under a H2 atmosphere (1 Atm) overnight. The resulting mixture was filtered through a pad of Celite® and the filtrate was concentrated under reduced pressure to give (±)-5-[(1R*)-3-(4-fluorophenyl)-1-hydroxypropyl](4R*,5R*)-1-methyl-4-phenylpyrrolidin-2-one (67 mg, 100%) as a white solid: mp 122-124° C.

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f853d134c96d4bcc97070a822ede0f3e
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

Loading…