Methyl morpholine oxide → 1-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile

HRID 1672503Notes

Reaction equation

HRID 1672503 reaction equation
[OH:1][CH:2]([CH:24]([O:26][CH2:27][O:28][CH3:29])[CH3:25])[CH2:3][N:4]1[C:9]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][C:7]([C:17]([F:20])([F:19])[F:18])=[C:6]([C:21]#[N:22])[C:5]1=[O:23].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:29][O:28][CH2:27][O:26][CH:24]([CH3:25])[C:2](=[O:1])[CH2:3][N:4]1[C:9]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][C:7]([C:17]([F:18])([F:19])[F:20])=[C:6]([C:21]#[N:22])[C:5]1=[O:23]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 673389801-(2-Hydroxy-3-methoxymethoxy-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile

Product 1

HCID 673402801-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrileYield 90%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(2-Hydroxy-3-methoxymethoxy-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile 29 (0.21 g, 0.52 mmoles) was combined with N-methylmorpholine N-oxide (NMO, 92 mg, 0.79 mmoles) and 4 Å molecular sieves (powder, 170 mg) in 5 mL of anhydrous DCM within a 7 mL reaction vial. The mixture was stirred at room temperature for 10 min. After this period tetrapropylammonium perruthenate (TPAP, 10 mg, 0.028 mmoles) was added and the mixture was stirred at room temperature for an additional 3 hours. After this period the reaction mixture was purified directly using flash silica chromatography (0-40% EtOAc/Hexane) to yield 0.191 g (90% yield) of 1-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile as a yellow residue.

Workup

  1. stirringthe mixture was stirred at room temperature for an additional 3 hours
  2. customAfter this period the reaction mixture was purified directly

Sources & evidence

ORD record
ord-aea83a1d4c4c483da26a634eea95f117
Source dataset
uspto-grants-2011_08
Patent number
US07998986B2

Reaction notes

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