Hydrochloric Acid → HCID 70047968, compound
Reaction equation
[CH2:1]([C@H:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH2:11][NH:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([C@H:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
10 ml of 1M borane/THF complex was added to 10 ml of a solution of 0.81 g (2.6 mmol) of trans-3-benzyl-4-(3,4-dimethoxyphenyl)-2-pyrrolidone in THF, and the mixture was heated under reflux for 6 hr. After the completion of the cooling, 10 ml of a 6N hydrochloric acid solution was dropwise added at room temperature carefully, and the mixture was stirred at 60° C. for 30 min. THF was distilled off in vacuo, and the residue was basified with a 10% aqueous sodium hydroxide solution and extracted twice with methylene chloride. The resultant organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off in vacuo to prepare a crude product. The crude product was adsorbed on silica gel to elute impurities (methylene:methanol=95:5), and elution was again conducted to prepare 0.37 g (yield: 48%) of an intended product.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 6 hr
- distillationTHF was distilled off in vacuo
- extractionextracted twice with methylene chloride
- dry with materialThe resultant organic phase was dried over anhydrous sodium sulfate
- distillationthe solvent was distilled off in vacuo
- customto prepare a crude product
- washto elute
- washimpurities (methylene:methanol=95:5), and elution
Sources & evidence
- ORD record
- ord-97b758ff035d48cd9c77ebdd17598fdf
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05444083
Reaction notes
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