Methyl morpholine oxide → HCID 58993130, compound

HRID 470918Notes

Reaction equation

HRID 470918 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH2:16][N:15]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH2:14][C:13]([CH3:28])([CH3:27])[C:12]=3[N:11]=[C:10]([CH:29]([CH3:31])[CH3:30])[C:9]=2[CH2:32][OH:33])=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH2:16][N:15]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])=[O:19])[CH2:14][C:13]([CH3:28])([CH3:27])[C:12]=3[N:11]=[C:10]([CH:29]([CH3:30])[CH3:31])[C:9]=2[CH:32]=[O:33])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58992982HCID 58992982, compound

Product 1

HCID 58993130HCID 58993130, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-(trimethylsilyl)ethyl 4-(4-fluorophenyl)-3-(hydroxymethyl)-2-isopropyl-8,8-dimethyl-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (4.73 g, 10 mmol), N-methylmorpholine-N-oxide (1.29 g, 11.00 mmol) and 4 Å molecular sieves (2 g) in CH2Cl2 (100 mL) was added tetrapropylammonium perruthenate (0.09 g, 0.25 mmol) at rt. After 5 h, the reaction mixture was diluted with hexanes (100 mL), filtered through a plug of silica gel using 1:1 Et2O/hexanes (500 mL) and concentrated under reduced pressure to afford 2-(trimethylsilyl)ethyl 4-(4-fluorophenyl)-3-formyl-2-isopropyl-8,8-dimethyl-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (4.28 g, 91% yield) as a pale yellow pasty solid. 1H NMR (500 MHz, CDCl3) δ ppm: 9.79 (1H, s), 7.18 (4H, d, J=6.4 Hz), 4.24 (2H, br. s.), 4.16 (2H, t, J=8.1 Hz), 3.54 (2H, br. s.), 1.36 (6H, s), 1.28 (6H, d, J=6.7 Hz), 1.22-1.27 (1H, m), 0.93-1.05 (1H, m), 0.84-0.93 (1H, m), 0.02 (9H, br. s.). LCMS (M+H) calcd for C26H36N2O3Si: 471.25. found: 471.3.

Workup

  1. filtrationfiltered through a plug of silica gel using 1:1 Et2O/hexanes (500 mL)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51f179c21d0b420abb59898997e705c4
Source dataset
uspto-grants-2014_01
Patent number
US08629276B2

Reaction notes

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