Potassium Hydroxide → HCID 67341449, compound
Reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.O=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1>CO>[C:25]([O:24][C:22]([N:19]1[CH2:18][CH:17]=[C:16]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:12]([OH:14])=[O:13])[CH:7]=3)[NH:3][CH:4]=2)[CH2:21][CH2:20]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Potassium hydroxide (5.17 g, 92.08 mmol) was added to 1H-indole-5-carboxylic acid (3.71 g, 23.02 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (9.17 g, 46.04 mmol) in methanol (80 mL) at ambient temperature and the resulting solution was stirred at 65° C. for 18 hours. The mixture was then cooled to ambient temperature, quenched in water (100 mL) and extracted with ethyl acetate (2×100 mL). The extracts were discarded and the aqueous phase acidified to pH 2-3 wth 2M hydrochloric acid to give a pale yellow solid. The solid was collected by filtration, washed sequentially with water and ether and air dried to give 3-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole-5-carboxylic acid (5.62 g, 71.3%) as a colourless solid.
Workup
- temperatureThe mixture was then cooled to ambient temperature
- customquenched in water (100 mL)
- extractionextracted with ethyl acetate (2×100 mL)
- customto give a pale yellow solid
- filtrationThe solid was collected by filtration
- washwashed sequentially with water and ether and air
- customdried
Sources & evidence
- ORD record
- ord-ed909740794c42c1a03dcfc8197c2fe3
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003649B2
Reaction notes
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