ethyl 1-aminocyclohexane-1-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of ethyl 1-aminocyclohexanecarboxylate (669 g), potassium carbonate (683.1 g) and ethyl 4-bromobutyrate (558 ml) was stirred at 130° C. for 18 hours, then cooled to ambient temperature and poured onto ice-water (3 l). The product was extracted into dichloromethane and the combined extracts were dried over sodium sulphate and the solvent was removed in vacuo to yield ethyl 1-(3-ethoxycarbonylpropylamino)cyclohexanecarboxylate as a brown/orange oil. Yield 943.2 g. cooled to ambient temperature poured onto ice-water (3 l) The product was extracted into dichloromethane the combined extracts were dried over sodium sulphate the solvent was removed in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethanol (4 l) was saturated at 0°-5° C. over 4 hours with hydrogen chloride. 1-Aminocyclohexanecarboxylic acid (600 g) was added in one portion and the mixture was stirred and heated under reflux for 8 hours, then allowed to stand at ambient temperature for 72 hours. The solvent was removed in vacuo and the residue was dissolved in ice-water (1 l) and basified to pH 8-9 at 0°-5° C. by the addition of 2M aqueous sodium hydroxide solution. The product was extracted into dichloromethane (4×300 ml) and the extracts were combined and dried over sodium sulphate. The aqueous residues were basified to pH 10 by the addition of more 2M aqueous sodium hydroxide solution and further product was extracted into dichloromethane (4×200 ml). The extracts were combined and dried over sodium sulphate. The dried dichloromethane extracts were combined and the solvent was removed in vacuo to leave ethyl 1-aminocyclohexanecarboxylate as a pale yellow oil. Yield 669 g. heated under reflux for 8 hours The solvent was removed in vacuo the residue was dissolved in ice-water (1 l) basified to pH 8-9 at 0°-5° C. by the addition of 2M aqueous sodium hydroxide solution The product was extracted into dichloromethane (4×300 ml) dried over sodium sulphate The aqueous residues were basified to pH 10 by the addition of more 2M aqueous sodium hydroxide solution and further product was extracted into dichloromethane (4×200 ml) dried over sodium sulphate the solvent was removed in vacuo

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of ethyl 1-aminocyclohexanecarboxylate (669 g), potassium carbonate (683.1 g) and ethyl 4-bromobutyrate (558 ml) was stirred at 130° C. for 18 hours, then cooled to ambient temperature and poured onto ice-water (3 l). The product was extracted into dichloromethane and the combined extracts were dried over sodium sulphate and the solvent was removed in vacuo to yield ethyl 1-(3-ethoxycarbonylpropylamino)cyclohexanecarboxylate as a brown/orange oil. Yield 943.2 g. cooled to ambient temperature poured onto ice-water (3 l) The product was extracted into dichloromethane the combined extracts were dried over sodium sulphate the solvent was removed in vacuo