Toluene → 1-tert-Butyl 2-methyl (2S,4R)-4-[(1-allyl-6-oxo-1,6-dihydropyridin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 1255525Notes

Reaction equation

HRID 1255525 reaction equation
C([O:4][C:5]1[N:10]=[C:9]([O:11][C@H:12]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)[CH:8]=[CH:7][CH:6]=1)C=C.[C:28]1(C)[CH:33]=CC=C[CH:29]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:33]([N:10]1[C:5](=[O:4])[CH:6]=[CH:7][CH:8]=[C:9]1[O:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1)[CH:28]=[CH2:29]

Participants

4

Reactant 2

HCID 1140TolueneHCID 581581101-tert-Butyl 2-methyl (2S,4R)-4-{[6-(allyloxy)pyridin-2-yl]oxy}pyrrolidine-1,2-dicarboxylate

Product 1

HCID 581580101-tert-Butyl 2-methyl (2S,4R)-4-[(1-allyl-6-oxo-1,6-dihydropyridin-2-yl)oxy]pyrrolidine-1,2-dicarboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

An oven-dried 100 mL Kjeldahl Flask under nitrogen was charged with the product of Step 5 (2.82 g, 7.45 mmol) and toluene (15 ml). Degassed 5 minutes with nitrogen. Added tetrakis(triphenylphosphine)palladium(0) (0.431 g, 0.373 mmol). Heated in a 60° C. oil bath for 1 hour. HPLC/MS shows product. HPLC/MS looks good after 2 hours. Cooled. Evaporated. Subjected to flash column chromatography eluting with 99 methylene chloride/1 methanol. Evaporation of fractions containing product gave the title compound as an oil/foam. (1.91 g, 5.05 mmol, 67,7% yield). LCMS (ES+) m/z 379.3 (M+H)+.

Workup

  1. customDegassed 5 minutes with nitrogen
  2. temperatureCooled
  3. customEvaporated
  4. washeluting with 99 methylene chloride/1 methanol
  5. customEvaporation of fractions
  6. additioncontaining product

Sources & evidence

ORD record
ord-75dd4ad89d5a4c4f8f39de5123da125a
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

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