Hydrochloric Acid → Benzyl 3-hydroxy-4-(4-hydroxyphenyl)piperidinecarboxylate
Reaction equation
[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])(C)C)=[O:16])[CH2:3]1.CO.Cl>C(Cl)(Cl)Cl>[OH:1][CH:2]1[CH:7]([C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][C:21]2[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)=[O:16])[CH2:3]1Participants
Conditions
- Temperature
- 60 °C
Procedure
The mixture of 6.0 g of tert-butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate, 120 ml of methanol, 40 ml of chloroform and 20 ml of 2M HCl is stirred at 60° C. over 20 hours. The reaction mixture is cooled and the organic solvent is evaporated off. The resulting aqueous solution is admixed with stirring with 80 ml of saturated sodium hydrogencarbonate solution and 80 ml of ethyl acetate. The biphasic mixture is cooled to 0° C. and admixed slowly with 3.30 ml of benzyl chloroformate and stirred over a further 2 hours. The reaction mixture is extracted with ethyl acetate-tetrahydrofuran. The organic phases are concentrated by evaporation and the title compound is obtained as a white solid from the residue by means of crystallization (ethyl acetate-heptane). Rt=5.72.
Workup
- temperatureThe reaction mixture is cooled
- customthe organic solvent is evaporated off
- stirringwith stirring with 80 ml of saturated sodium hydrogencarbonate solution and 80 ml of ethyl acetate
- temperatureThe biphasic mixture is cooled to 0° C.
- stirringstirred over a further 2 hours
- extractionThe reaction mixture is extracted with ethyl acetate-tetrahydrofuran
- concentrationThe organic phases are concentrated by evaporation
Sources & evidence
- ORD record
- ord-7086bb1acdab494d80527fa7b94c5278
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790715B2
Reaction notes
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