HCID 68896195, compound → HCID 68896125, compound

HRID 1394931Notes

Reaction equation

HRID 1394931 reaction equation
[CH2:1]([N:4]([C:12]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:13]=C)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=C>C(Cl)Cl>[CH3:13][C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:21]=[CH:2][CH2:1][N:4]1[C:5]([O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[O:11]

Participants

3

Reactant 1

HCID 68896195HCID 68896195, compound

Product 1

HCID 68896125HCID 68896125, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 20-3 (0.78 g, 2.7 mmol) and tricyclohexylphosphine[1,3-bis(2,4,6-trinmethylphenyl)-4,5-dihydroimidazol-2-ylidene][benylidine]ruthenium (IV)dichloroide (0.04 g, 0.05 mmol) in CH2Cl2 (500 mL) was stirred 1 hour. at 40° C. under N2. The reaction mixture was concentrated under reduced pressure and purified by flash column chromotography (SiO2, O-30% EtOAc/Hexanes gradient) to give tert-butyl 2-methyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate, 20-4. 1H NMR (300 MHz, CDCl3) δ 7.25 (m, 5H), 5.79 (m, 1H), 5.58 (m, 1H), 4.32 (m, 1H), 4.43 (m, 1H), 1.8 (s, 3H), 1.5 (s, 9H); LRMS m/z (M+H) 260.1 found, 260.2 required.

Workup

  1. customat 40° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by flash column chromotography (SiO2

Sources & evidence

ORD record
ord-d64687b774cd4e6580866fd22914921e
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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