Hydrochloric Acid → 4-Methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].Cl>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:10][CH:9]1[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
The 4-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester (110.89 mg, 0.55 mmol) was dissolved in anhydrous DCM and triethylamine (166.96 mg, 1.65 mmol, 0.23 mL) was added under argon. The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (69.30 mg, 0.61 mmol, 0.05 mL) was added via syringe. The reaction was stirred at 0° C. for 30 min and then allowed to warm to room temp and stir for 12 h. The reaction was slowly poured into a 1N HCl solution and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (3:1 hexane-ethyl acetate) Yield 135.21 mg.
Workup
- temperatureto warm to room temp
- stirringstir for 12 h
- extractionthe aqueous layer was extracted three times with ethyl acetate
- washThe combined organic layers were washed with water and brine
- dry with materialthen dried over MgSO4
- filtrationThe solution was filtered
- customthe solvent removed under reduced pressure
- customThe product was isolated by flash chromatography
Sources & evidence
- ORD record
- ord-11707eb308254c3e8220457f94ec06db
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06906067B2
Reaction notes
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