Methyl morpholine oxide → (1R,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropanecarbaldehyde
Reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][OH:19])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH:18]=[O:19])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A mixture of the product of step A (5 g, 19.6 mmol), powdered 4 Å activated molecular sieves (10 g) and N-methylmorpholine oxide (3.5 g, 29.4 mmol) was stirred in DCM (100 mL) for 15 min at RT. Then the mixture was cooled to 0° C. and tetrapropylammonium perruthenate (0.69 g, 0.196 mmol) was added in one portion. The cold bath was removed and the mixture was stirred at RT for 1 h. The reaction was diluted with Et2O and stirred for 15 min at RT. The mixture was filtered through a plug of silica gel which was washed thoroughly with 2:1 hexane: ethyl acetate. The filtrate was concentrated to get a residue which was purified by column chromatography on silica (elution with 2:1 hexane:ethyl acetate) to yield the desired aldehyde. MS (ESI) m/z 260 [M+H]+.
Workup
- customThe cold bath was removed
- additionThe reaction was diluted with Et2O
- stirringstirred for 15 min at RT
- filtrationThe mixture was filtered through a plug of silica gel which
- washwas washed thoroughly with 2:1 hexane
- concentrationThe filtrate was concentrated
- customto get a residue which
- customwas purified by column chromatography on silica (elution with 2:1 hexane:ethyl acetate)
Sources & evidence
- ORD record
- ord-76fb775e543b4018b16b28459f5e1642
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006228B2
Reaction notes
Loading…