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PROCESS FOR PREPARATION OF BETA-AMINOESTERS

IP.com Disclosure Number: IPCOM000253907D
Publication Date: 2018-May-15
Document File: 1 page(s) / 230K

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PROCESS FOR PREPARATION OF BETA-AMINOESTERS

Chiral amine hydrochloride (compound (I), 15.00 g) was dissolved in toluene (150 mL) and 10 % NaOCl (63.6 mL) was added while stirring vigorously. Reaction mixture was heated at 65 °C for 2 hours. After the reaction was finished, reaction mixture was cooled to room temperature and phases were separated. To the organic phase NaOH(aq) (8.48 g NaOH(s) + 45 mL H2O) and DBN (12 mol-% relative to compound (I)) were added while stirring vigorously. Reaction mixture was stirred at room temperature for another 21 hours. After the reaction was finished, phases were separated and toluene was evaporated under vacuum. Crude enamine was dissolved in toluene (120 mL) and cooled on ice bath (0 °C). While stirring, NaBH4 (4.01 g) was added and then AcOH (24 mL) was added slowly during 15 min. Reaction mixture was stirred at 0 °C for another 5 minutes, then left to warm to room temperature and stirred for another hour. Afterwards it was cooled to 0 °C again and while stirring vigorously, saturated NaHCO3 solution (120 mL) and K2CO3 were added slowly to pH = 8.6. Phases were separated and water phase was extracted with toluene (2 × 25 mL). Organic phases were combined and washed with 5 % NaCl solution. Toluene was evaporated under vacuum. m (racemic amine, compound (II)) = 10.88 g Compound (II) can be resolved into its enantiomers by conventional methods such as diastereomeric salt formation with a chiral resolving agent as described in PCT patent ap...