Methanol → 1-(3-Methylcyclohexyl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid
Reaction equation
O=[C:2]1[O:7][CH:6]=[C:5]([C:8]([O:10]C)=[O:9])[CH:4]=[CH:3]1.[CH3:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH:15]([NH2:19])[CH2:14]1.CO.[Li+].[OH-]>C1COCC1>[CH3:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH:15]([N:19]2[C:2](=[O:7])[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6]2)[CH2:14]1Participants
Procedure
A solution of methyl 6-oxo-6H-pyran-3-carboxylate (620 mg, 4.0 mmol, Aldrich) and 3-methylcyclohexanamine (900 mg, 8.0 mmol, Pfaltz and Bauer) was heated in the Emry's optimizer microwave at 150° C. for 15 min. The resulting solution was transferred to a 50 mL round bottom flask with THF, then diluted with THF:MeOH to give approximately 40 mL of a 3:1 THF:MeOH solution. Add 1 M LiOH (6 mL, 6 mmol) and stir at RT overnight. The solution was concentrated in vacuo and the residue taken up in H2O. The aqueous solution was extracted with ether (30 mL). 2 N HCl was added to acidify the aqueous solution to pH 2. The aqueous solution was extracted with EtOAc (3×) and the combined EtOAc layers dried over MgSO4, and concentrated in vacuo to give 200 mg (21%) of the desired product as a light brown residue. MS m/z: 612.5(M+1).
Workup
- concentrationThe solution was concentrated in vacuo
- extractionThe aqueous solution was extracted with ether (30 mL)
- addition2 N HCl was added
- extractionThe aqueous solution was extracted with EtOAc (3×)
- dry with materialthe combined EtOAc layers dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4a56ac120f624ac3b148a49a2eec63b7
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872009B2
Reaction notes
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