Hydrochloric Acid → 4-Acetyl-1-[(1S)-1-(4-methoxyphenyl)ethyl]pyrrolidin-2-one
Reaction equation
[CH3:1][Mg]Br.CON[C:7]([CH:9]1[CH2:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH3:16])[CH2:10]1)=[O:8].Cl>C(OCC)C.CC1CCCO1>[C:7]([CH:9]1[CH2:10][N:11]([C@H:15]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH3:16])[C:12](=[O:14])[CH2:13]1)(=[O:8])[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
530 mL of a 3 M solution of methylmagnesium bromide in diethylether is added slowly to a cooled solution of 271 g of (R/S)—N-Methoxy-5-oxo-1-[(S)-1-(4-methoxyphenyl)-ethyl]-pyrrolidine-3-carboxamide (mixture of diastereoisomers) in 1.4 L of 2-methyltetrahydrofuran so that the temperature remains under 0° C. After complete addition the temperature is kept for 75 minutes at 0° C. and then warmed up to 20° C. The suspension is stirred 16 hours at 20° C. Under cooling 650 mL of a 4 M hydrochloric acid are added. The organic phase is separated and washed with 500 mL saturated sodium carbonate solution and with 500 mL saturated brine. The organic phase is dried over sodium sulfate. After filtration the solvent is evaporated under reduced pressure.
Workup
- customremains under 0° C
- additionAfter complete addition the temperature
- additionare added
- customThe organic phase is separated
- washwashed with 500 mL saturated sodium carbonate solution and with 500 mL saturated brine
- dry with materialThe organic phase is dried over sodium sulfate
- filtrationAfter filtration the solvent
- customis evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-ec352a7eae25486aaccf496bba63379c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187478B2
Reaction notes
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