Methanol → HCID 178501195, compound
Reaction equation
S(Cl)(Cl)=O.Cl.[C:6]1([NH:12][C@@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:22]O>>[C:6]1([NH:12][C@@H:13]2[CH2:14][CH2:15][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1Participants
Procedure
Thionyl chloride (0.65 g, 5.47 mmol) was added to a stirred solution of cis-4-(phenylamino)cyclohexanecarboxylic acid hydrochloride (600 mg, 2.74 mmol) in MeOH (10 ml) at room temperature and heated at reflux for 5 h. The reaction mixture was concentrated under reduced pressure. The crude product was basified with saturated sodium bicarbonate solution and extracted with DCM (2×25 ml). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude compound which was purified by column chromatography over neutral alumina by eluting in 10% ethyl acetate in petroleum ether to afford 500 mg of cis-methyl 4-(phenylamino)cyclohexanecarboxylate (78%) as colorless oily liquid.
Workup
- temperatureheated
- temperatureat reflux for 5 h
- concentrationThe reaction mixture was concentrated under reduced pressure
- extractionextracted with DCM (2×25 ml)
- washThe combined organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto afford the crude compound which
- customwas purified by column chromatography over neutral alumina
- washby eluting in 10% ethyl acetate in petroleum ether
Sources & evidence
- ORD record
- ord-79ba6ef747824df985e14318ffc25857
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518948B2
Reaction notes
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