Hydrochloric Acid → 4-Aminotetrahydropyran-4-carboxylic acid benzyl ester
Reaction equation
[CH2:1]([O:8][C:9]([C:11]1([N:17]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(OCC)C>[CH2:1]([O:8][C:9]([C:11]1([NH2:17])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
To a solution of 4-[N-(diphenylmethylene)amino]tetrahydropyran-4-carboxylic acid benzyl ester (0.047 mole) in diethyl ether (120 mL) is added 1M aqueous hydrochloric acid solution (100 mL). The mixture is stirred vigorously at room temperature for 16 hours. The layers are separated and the aqueous layer washed with diethyl ether. The aqueous layer is brought to pH 10 with dilute aqueous ammonium hydroxide solution and extracted with dichloromethane. The organic extract is dried over sodium sulfate and concentrated to give 4-aminotetrahydropyran-4-carboxylic acid benzyl ester.