Imidazole → methyl (2S,4R)-4-(tert-butyl(dimethyl)silyl)oxy-1-methyl-pyrrolidine-2-carboxylate
Reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([CH3:7])[C@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>ClCCl>[Si:21]([O:1][C@H:2]1[CH2:6][N:5]([CH3:7])[C@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23]Participants
Procedure
Methyl (2S,4R)-4-hydroxy-1-methyl-pyrrolidine-2-carboxylate 3b (6 g, 37 mmol) was dissolved in 100 mL of dichloromethane, followed by addition of imidazole (7.70 g, 113 mmol) and tert-butyl dimethylchlorosilane (6.80 g, 45 mmol) successively. After stirring for 12 hours, the reaction mixture was diluted with 100 mL of dichloromethane, washed with water (50 mL) and saturated brine (50 mL) successively, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography with elution system A to obtain the title compound methyl (2S,4R)-4-(tert-butyl(dimethyl)silyl)oxy-1-methyl-pyrrolidine-2-carboxylate 3c crude product as a colourless oil, which was directly used in the next step without purification.
Workup
- washwashed with water (50 mL) and saturated brine (50 mL) successively
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography with elution system
Sources & evidence
- ORD record
- ord-9710ce6dd21c4ebc92dbd8d6d1316c02
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09358227B2
Reaction notes
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