Hydrochloric Acid → HCID 11437182, compound

HRID 537371Notes

Reaction equation

HRID 537371 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH:9]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][C:17](Cl)=[O:18])=[CH:11][CH:10]=1.Cl.[CH2:21]1[CH2:25]OC[CH2:22]1>CCOCC>[CH2:25]([CH:7]1[CH2:8][C:3](=[O:2])[CH:4]=[CH:5][N:6]1[C:17]([O:16][CH2:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)=[O:18])[CH:21]=[CH2:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 692784-Methoxypyridine

Product 1

HCID 11437182HCID 11437182, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-23 °C

Procedure

At −23° C., to a solution of 4-methoxypyridine (5.45 g, 50 mmol) in THF (50 mL), 1.0 N Allyl-MgBr (50 mL, 50 mmol) in ether was added to form a yellow suspension. 95% Cbz-Cl (7.4 mL, 50 mmol) was then added dropwise. The yellow mixture was stirred at −23° C. for 30 mins and then poured into 10% HCl (100 mL). The reaction mixture was extracted with ethyl acetate. After removal of solvent, the crude product was purified by silica gel chromatography (gradient, 10% to 25% EtOAc/hexanes) to give benzyl 2-allyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate 129. LC/MS RT (2.25 min method)=1.090 min. Mass observed: 272.1 (M+H).

Workup

  1. customto form a yellow suspension
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. customAfter removal of solvent
  4. customthe crude product was purified by silica gel chromatography (gradient, 10% to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0f8e1f17bef04df9a7ab2404b4c41406
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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