Pyridine → HCID 59066460, compound

HRID 1838000Notes

Reaction equation

HRID 1838000 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].N1C=CC=CC=1>[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](/[CH:8]=[CH: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 3

HCID 1049PyridineHCID 5226271-Ethynyl-4-fluorobenzeneHCID 13825985(-)-(4R*,5R*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one

Product 2

HCID 9858383HCID 9858383, compoundHCID 59066460HCID 59066460, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(±)-(4R*,5R*)-5-[(1R*)-3-(4-Fluorophenyl)-1-hydroxyprop-2-ynyl]-1-methyl-4-phenylpyrrolidin-2-one was prepared from 4-fluorophenylacetylene and Intermediate Z using a method analogous to that described for Example 8. To a 300 mg (0.93 mmol)slurry of this compound in hexanes (60 mL) was added Pd on CaCO3 (80 Mg), followed by pyridine (0.23 mL, 2.8 mmol). The reaction mixture was stir-red overnight, then filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give (±)-(4R*,5R*)-5-[(2Z)(1R*)-3-(4-fluorophenyl)-1-hydroxyprop-2-enyl]-1-methyl-4-phenylpyrrolidin-2-one (302 mg, 100%) as a white solid: mp 163-165° C.; 1H NMR (CD3OD) δ 2.36 (dd, J=15.8, 7.8 Hz, 1H), 3.01-3.17 (m, 4H), 3.80-3.90 (m, 2H), 4.33 (d, J=8.7 Hz, 1H), 5.74 (dd, J=11.6, 8.8 Hz, 1H), 6.34 (d, J=11.6 Hz, 1H), 6.85-6.97 (m, 4H), 7.18-7.36 (m, 5H).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-24c31f87b0d44808a1ed7b86e786657d
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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