Triethylamine → rel-1,1-Dimethylethyl (3R,4S)-3-amino-4-(3,4-dichlorophenyl)-1-pyrrolidinecarboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[C@@H:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P([N:38]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C(N(CC)CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[NH2:38][C@@H:10]1[C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of the compound (14.4 g) obtained in step 5 in toluene (120 mL) were added DPPA (16.5 g) and triethylamine (8.36 mL) at room temperature, and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was cooled, 8N aqueous sodium hydroxide solution (50 mL) was added, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and brine and dried, and the solvent was evaporated under reduced pressure to give crude tert-butyl (3R*,4S*)-3-amino-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate (13.3 g, 100%) as a brown oil.
Workup
- temperatureThe reaction mixture was cooled
- stirringthe mixture was stirred at room temperature for 14 hr
- extractionthe resultant product was extracted with ethyl acetate
- washThe organic layer was washed with saturated aqueous ammonium chloride solution and brine
- customdried
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-a87075bbe20f4a5b8da308e9febcfbfc
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470816B2
Reaction notes
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