2-Pyridinemethanamine → HCID 14621504, compound
Reaction equation
[CH:1]([C@H:3]1[C@@H:8]([CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][O:6][C@@H:5]([CH3:19])[O:4]1)=O.[NH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[CH3:18][O:17][C:15]([CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][C@H:8]1[CH2:7][O:6][C@@H:5]([CH3:19])[O:4][C@H:3]1[CH2:1][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=[O:16]Participants
Procedure
To a mixture of (2R,4R,5S)-4-formyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (200 mg) and 2-aminomethylpyridine (0.15 ml) in a mixture of methanol (4 ml) and acetic acid (1 ml) was added sodium cyanoborohydride (100 ml) and the solution was stirred at room temperature overnight. The mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with chloroform. The organic extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column (10 g) with a mixture of chloroform and methanol (30:1) as an eluent to give (2R,4R,5S)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-4-(2-pyridylmethylaminomethyl)-1,3-dioxane (165 mg).
Workup
- extractionextracted with chloroform
- extractionThe organic extract
- washwas washed with brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated in vacuo
- customthe residue was chromatographed on a silica gel column (10 g) with a mixture of chloroform and methanol (30:1) as an eluent
Sources & evidence
- ORD record
- ord-2c3d2bc697bb4ee3a3a1954fa90f5aca
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04929639
Reaction notes
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