Dimethylformamide → cis-5-Methoxymethyl-3-Cyano-Cbz-Pyrrolidine
Reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[N:8]([C:9]([O:11][C:12]([CH3:15])(C)C)=[O:10])[CH2:7][C@@H:6]([C:16](O)=O)[CH2:5]1.[CH2:19](Br)[C:20]1C=C[CH:23]=[CH:22][CH:21]=1.C[N:28](C=O)C>>[CH3:1][O:2][CH2:3][C@H:4]1[N:8]([C:9]([O:11][CH2:12][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:10])[CH2:7][C@@H:6]([C:16]#[N:28])[CH2:5]1Participants
4
Procedure
cis-5-Methoxymethyl-Boc-3-Pyrrolidine Benzyl Ester Acid {cis-Boc-(5-MOM)-PCA-OBn} 4.8. cis-5-Methoxymethyl-Boc-3-pyrrolidine carboxylic acid (1.4 g, 5.3 mmol) was dissolved in DMF (26.5 mL). CS2CO3 (1.73 g, 5.3 mmol) and benzyl bromide (0.76 mL, 6.4 mmol) were added, and the reaction mixture was stirred 24 h at room temperature. The reaction mixture was concentrated, and the residue was dissolved in H2O. The aqueous solution was extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate/hexanes (1/1, v/v) to afford 1.88 g (85% yield) of the desired product as an oil.
Workup
- concentrationThe reaction mixture was concentrated
- dissolutionthe residue was dissolved in H2O
- extractionThe aqueous solution was extracted with ethyl acetate
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
- customThe crude product was purified by column chromatography
- washeluting with ethyl acetate/hexanes (1/1
Sources & evidence
- ORD record
- ord-9b33f416771a497db69dcb2a77bfb9cb
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06710186B2
Reaction notes
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