Ammonium Chloride → HCID 22031589, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH:15]([CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1)=[O:16].[Cl-].[NH4+]>O1CCCC1.CCCCCC.O>[OH:16][CH:15]([C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1)[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
380 mg of 1-bromo-4-methylsulfanyl benzene was dissolved in 10 mL anhydrous tetrahydrofuran, and 1.24 mL solution of 1.59 M n-butyl lithium in hexane was added dropwise thereto at −70° C. After the mixture was stirred for 1 hour, 3 mL solution of 400 mg t-butyl 4-formyl-piperidine-1-carboxylate in anhydrous tetrahydrofuran was added dropwise thereto, and the mixture was stirred at −70° C. for 2 hours. The temperature of the reaction mixture was increased gradually to 0° C., then water and an ammonium chloride solution were added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and purified by silica gel column chromatography (ethyl acetate/hexane) to give 150 mg of the title compound as a colorless amorphous.
Workup
- customat −70° C
- stirringthe mixture was stirred at −70° C. for 2 hours
- extractionthe reaction mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over magnesium sulfate
- custompurified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-4e23a5fb633e499fab4435e476f56b52
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074801B1
Reaction notes
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