tert-Butyl 4-[(3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-1-[(2,6-dichlorophenyl)methyl]-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate → tert-Butyl 4-[(3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-1-[(2,6-dichlorophenyl)methyl]-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6](=[O:39])[CH2:7][C:8]1([C:23]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)=[O:24])[CH:12]([CH3:13])[CH2:11][N:10]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CCCCCC.C(O)C>[C:1]([O:5][C:6](=[O:39])[CH2:7][C@@:8]1([C:23]([NH:25][CH:26]2[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]2)=[O:24])[C@H:12]([CH3:13])[CH2:11][N:10]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl 4-[(3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-1-[(2,6-dichlorophenyl)methyl]-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate obtained in Example 5a (2.04 g, 3.49 mmol) was optically resolved repeatedly by HPLC (CHIRALPAK IA (3 cm diameter×25 cm), elution solvent: hexane/ethanol=94/6, flow rate: 22 ml/min.) to give the title compound (a chiral form corresponding to the peak with a shorter retention time) (859 mg, 42.1%) and the optical isomer (a chiral form corresponding to the peak with a longer retention time) (817 mg, 40%), respectively.
Sources & evidence
- ORD record
- ord-72860b60df24498293350464a6e7960a
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476301B2
Reaction notes
Loading…