Tributylphosphine → (R)-methyl 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylate

HRID 1501205Notes

Reaction equation

HRID 1501205 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]1([C@@H:18](O)[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[O:1]=[C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][N:11]1[C@@H:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:19]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 4431351-Phenylethanol, (S)-HCID 178498433HCID 178498433, compound

Product 1

HCID 89585124(R)-methyl 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylateYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-hydroxyisonicotinate (459 mg, 3 mmol) and (S)-1-phenylethanol (366 mg, 3 mmol) in tetrahydrofuran (30 mL) was added dropwise a solution of tributylphosphine (909 mg, 4.5 mmol) in tetrahydrofuran (10 mL). The reaction solution was stirred at 0° C. for 0.5 hours. To the above solution was added 1,1′-(Azodicarbonyl)-dipiperidine (1134 mg, 4.5 mmol). The reaction mixture was stirred at 0° C. for 0.5 hours. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give (R)-methyl 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylate as a white solid (451 mg, 58%).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 0.5 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3126e0a297214fe8bec7d01f33ce432b
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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