Azobisisobutyronitrile → HCID 59066463, compound

HRID 1838001Notes

Reaction equation

HRID 1838001 reaction equation
[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.CC(N=NC(C#N)(C)C)(C#N)C.C1(S)C=CC=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][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:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[OH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7969ThiophenolHCID 59066460HCID 59066460, compound

Product 1

HCID 59066463HCID 59066463, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (±)-5-[(2Z)(1R*)-3-(4-fluorophenyl)-1-hydroxyprop-2-enyl](4R*,5R*)-1-methyl-4-phenylpyrrolidin-2-one (115 mg, 0.35 mmol), AIBN (10 mg, 0.06 mmol) and thiophenol (12 mg, 0.11 mmol) in benzene (10 mL) was heated at the reflux temperature for 4 h. The resulting mixture was concentrated under reduced pressure and purified by preparatory TLC (90% EtoAc/hex) to give (±)-(4R*,5R*)-5-[(2E)(1R*)-3-(4-fluorophenyl)-1-hydroxyprop-2-enyl]-1-methyl-4-phenylpyrrolidin-2-one (30 mg, 26%) as a white solid: mp 189-191° C.; 1H NMR (CDCl3) δ 2.49-2.57 (m, 1H), 2.98 (s, 3H), 3.12-3.21 (m, 1H), 3.84-3.89 (m, 2H), 4.09-4.14 (m, 1H), 6.07 (dd, J=16.2, 5.0 Hz, 1H), 6.40 (dd, J=16.2, 1.7 Hz, 1H), 6.97-7.03 (m, 2H), 7.21-7.42 (m, 7H).

Workup

  1. temperaturewas heated at the reflux temperature for 4 h
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. custompurified by preparatory TLC (90% EtoAc/hex)

Sources & evidence

ORD record
ord-01fa88158e0d4da9b20f8394f263c2c9
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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