Methyl morpholine oxide → HCID 10361910, compound

HRID 1786165Notes

Reaction equation

HRID 1786165 reaction equation
[OH:1][C@@H:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:3][N:4]1[C:9]2([CH2:11][CH2:10]2)[CH2:8][CH2:7][N:6]2[C:12](=[O:22])[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[N:15]=[C:5]12.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]=[C:2]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:3][N:4]1[C:9]2([CH2:11][CH2:10]2)[CH2:8][CH2:7][N:6]2[C:12](=[O:22])[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[N:15]=[C:5]12

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 9885910HCID 9885910, compound

Product 1

HCID 10361910HCID 10361910, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

0.31 g (0.83 mmol) of 1′-[(2S)-2-hydroxy-2-phenylethyl]-8′-pyridin-4-yl-3′,4′-dihydrospiro[cyclopropane-1,2′-pyrimido[1,2-a]pyrimidin]-6′(1′H)-one was dissolved in 8 ml of anhydrous dichloromethane and mixed with 0.145 g (1.24 mmol) of N-methylmorpholine N-oxide, 0.003 g (0.0083 mmol) of tetra-n-propylammonium perruthenate and 1 g of powdered molecular sieves (4A). The mixture was stirred at 20° C. under nitrogen atmosphere for 12 h. The mixture was filtered. The filtrate was washed with a saturated aqueous solution of ammonium chloride, dried and evaporated to give crude product. Purification by chromatography on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 100/0 to 95/5 gave the compound in the form of free base which was transformed into its hydrochloride salt to give 0.078 g of pure product.

Workup

  1. filtrationThe mixture was filtered
  2. washThe filtrate was washed with a saturated aqueous solution of ammonium chloride
  3. customdried
  4. customevaporated
  5. customto give crude product
  6. customPurification by chromatography on silica gel eluting
  7. additionwith a mixture of dichloromethane/methanol in the proportions 100/0 to 95/5
  8. customgave the compound in the form of free base which

Sources & evidence

ORD record
ord-bcd291d62cbb4cc4bfa2c1d100e42272
Source dataset
uspto-grants-2009_03
Patent number
US07507743B2

Reaction notes

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