2-Naphthalenesulfonyl chloride → 4-Hydroxy-1-(naphthalene-2-sulfonyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
Reaction equation
Cl.[CH2:2]([O:4][C:5]([CH:7]1[C:12](=[O:13])[CH2:11][CH2:10][NH:9][CH2:8]1)=[O:6])[CH3:3].[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24](Cl)(=[O:26])=[O:25]>C[Si](C)(C)N[Si](C)(C)C.C1COCC1>[CH2:2]([O:4][C:5]([C:7]1[CH2:8][N:9]([S:24]([C:15]2[CH:16]=[CH:17][C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)(=[O:26])=[O:25])[CH2:10][CH2:11][C:12]=1[OH:13])=[O:6])[CH3:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
A suspension of 31.15 g (150 mmol) 3-Ethoxycarbonyl-4-piperidone hydrochloride was suspended in 400 ml hexamethyldisilazane and heated under reflux (140° C.) for 2.5 h. The solution was evaporated complete, the residue dissolved in 400 ml THF and treated with 34 g (150 mmol) of naphthalene-2-sulfonylchloride in 150 ml THF. The reaction was stirred 16 h at room temperature, evaporated, treated with 400 ml aqueous 10% NaCl, stirred for 10 min and extracted with EtOAc (3×400 ml). The organic phase was dried (Na2SO4) and evaporated and crystallized from Et2O at 5° C. to give 53.1 g (90%) of 4-hydroxy-1-(naphthalene-2-sulfonyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester, MS: 362 (MH+).
Workup
- temperatureheated
- customThe solution was evaporated complete
- dissolutionthe residue dissolved in 400 ml THF
- customevaporated
- additiontreated with 400 ml aqueous 10% NaCl
- stirringstirred for 10 min
- extractionextracted with EtOAc (3×400 ml)
- dry with materialThe organic phase was dried (Na2SO4)
- customevaporated
- customcrystallized from Et2O at 5° C.
Sources & evidence
- ORD record
- ord-5b798cdf8ee94f53ae60e11e60566366
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189756B2
Reaction notes
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