Toluene → HCID 86666309, compound

HRID 1026323Notes

Reaction equation

HRID 1026323 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:22])[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](OC)=[O:19])=[N:16][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:18]([C:15]1[N:16]=[CH:17][C:12]([O:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:22])=[CH:13][CH:14]=1)=[O:19]

Participants

6

Reactant 4

HCID 1140TolueneHCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 67777657HCID 67777657, compound

Product 1

HCID 86666309HCID 86666309, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of methyl 5-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)pyridine-2-carboxylate (4.78 g) in THF (75 mL) was added a toluene solution (1.0 M, 30.8 mL) of diisobutylaluminum hydride at −78° C., and the mixture was stirred at −20° C. for 2 hr under an argon atmosphere. Sodium sulfate decahydrate (22.7 g) was added thereto at −78° C., and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, and the solvent of the filtrate was evaporated under reduced pressure to give the title compound as a pale-yellow solid (4.30 g).

Workup

  1. stirringat −78° C., and the mixture was stirred at room temperature overnight
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe solvent of the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b10f9f743e004118b8fb30fe4f24bd61
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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