(2-Amino-6-methoxymethyl-pyridin-3-yl)methanol → 2-Amino-6-methoxymethyl-pyridine-3-carbaldehyde
Reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([CH2:10][O:11][CH3:12])[N:3]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([CH2:10][O:11][CH3:12])[N:3]=1Participants
4
Procedure
To a mixture of (2-amino-6-methoxymethyl-pyridin-3-yl)methanol (260 mg, 1.5 mmol) described in Manufacturing Example 26-1-5 and methylene chloride (15 mL) was added manganese dioxide (1.3 g, 15 mmol), which was stirred overnight at room temperature. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=3:2) to obtain the title compound (210 mg, 81%).
Workup
- filtrationThe reaction mixture was filtered through a Celite pad
- concentrationthe filtrate was concentrated under a reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=3:2)
Sources & evidence
- ORD record
- ord-f6edec80f2d9427d9b453cbd4ff41425
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158657B2
Reaction notes
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