Hydrochloric Acid → (R)-N-methoxy-1-((R)-1-(4-methoxyphenyl)ethyl)-N-methyl-5-oxopyrrolidine-3-carboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([N:11]2[C:15](=[O:16])[CH2:14][C@@H:13]([C:17]([OH:19])=O)[CH2:12]2)[CH3:10])=[CH:5][CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.C(N(C(C)C)CC)(C)C.[CH3:41][NH:42][O:43][CH3:44].Cl>CC1OCCC1>[CH3:44][O:43][N:42]([CH3:41])[C:17]([C@@H:13]1[CH2:14][C:15](=[O:16])[N:11]([C@@H:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH3:10])[CH2:12]1)=[O:19]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of (R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carboxylic acid 1.01 (1.0 g, 3.80 mmol) in 2-MeTHF (5 mL) was added CDI (925 mg, 5.70 mmol) and the mixture was stirred for 75 minutes over which time the reaction became homogenous. Diisopropylethyl amine (800 μL, 4.56 mmol) and N,O-dimethylhydroxylamine (445 mg, 4.56 mmol) were added and the reaction was stirred for 3 hours. 3M HCl (4 mL, 12 mmol) was added and the mixture was stirred for 5 minutes. The layers were separated, and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were dried (MgSO4), filtered and concentrated to afford (R)-N-methoxy-1-((R)-1-(4-methoxyphenyl)ethyl)-N-methyl-5-oxopyrrolidine-3-carboxamide 1.02.
Workup
- stirringthe reaction was stirred for 3 hours
- stirringthe mixture was stirred for 5 minutes
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
- dry with materialThe combined organics were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e94176b9a2bf4d46a70645a64a00ead4
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376441B2
Reaction notes
Loading…