Sodium Methoxide → HCID 70358178, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][N:7]([CH2:12][C:13]1[C:16]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=2[CH:14]=1)[CH2:8][CH2:9][CH:10]=[O:11])[CH3:2].C[O-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C@H:5]1[C@H:10]([OH:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[C:16]3[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=3[CH:14]=2)[CH2:6]1)=[O:23])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A solution of 12.78 g (40 mmol) of 3-[N-(5-methoxybenzocyclobuten-1-ylmethyl)-N-(3-oxopropyl)-amino]propionic acid ethyl ester in 100 ml of dimethylformamide is added to a solution of 2.43 g (45 mmol) of sodium methoxide in 15 ml of dimethylformamide and the whole is stirred for 3 hours at 40° C. The solvent is then evaporated off under reduced pressure and the residue is separated into its components by chromatography on 400 g of silica gel with dichloromethane/methanol (95:5). Trans-4-hydroxy-1-[(5-methoxybenzocyclobuten-1-yl)methyl]-piperidine-3-carboxylic acid ethyl ester is isolated first and then cis-4-hydroxy-1-[(5-methoxy- benzocyclobuten-1-yl)methyl]-piperidine-3-carboxylic acid ethyl ester the hydrochloride of which has a melting point of 156°-160° C.
Workup
- customThe solvent is then evaporated off under reduced pressure
- customthe residue is separated into its components by chromatography on 400 g of silica gel with dichloromethane/methanol (95:5)
Sources & evidence
- ORD record
- ord-f92427b7ec004206817ed6f144225c0a
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04833169
Reaction notes
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