6-Hydroxy-2-methylquinoline → HCID 178422868, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[C:13]([C@@H:17]1[CH2:22][CH2:21][C@H:20](O)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]>>[C:13]([C@H:17]1[CH2:22][CH2:21][C@H:20]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]3)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]Participants
3
Procedure
6-hydroxy-2-methylquinoline was treated with cis-4-tert-butylcyclohexanol under Mitsunobu conditions, affording 6-((trans)-4-tert-butylcyclohexyloxy)-2-methylquinoline, which in turn was oxidized with tert-butyl hydrogen peroxide and selenium dioxide in dioxane, providing 6-((trans)-4-tert-butylcyclohexyloxy)-2-formylquinoline. This aldehyde was then treated with t-butyl 3-aminopropionate and sodium cyanoborohydride in dichloroethane to afford t-butyl 3-(((6-(trans)-4-tert-butylcyclohexyloxy)-quinolin-2-yl)methyl)amino)propionate. Treatment with lithium hydroxide in methanol/THF gave the title compound, 3-((6-trans)-4-tert-butylcyclohexyloxy)quinolin-2-yl)methylamino)propanoic acid.
Sources & evidence
- ORD record
- ord-206c43ad110f46e2a6db79885747e222
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09186367B2
Reaction notes
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