Water → 4-Azido-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH:9]1[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+].O.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:19]=[N+:20]=[N-:21])[CH2:10][CH:9]1[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
The 4-methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester (135.21 mg, 0.48 mmol) was taken up in dry DMF under argon and sodium azide (156.00 mg, 2.40 mmol) was added. The reaction was then heated to 60° C. for 48 h. The reaction was poured into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with sat NaHCO3 and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (5:1 hexane-ethyl acetate) Yield 93.41 mg.
Workup
- extractionthe aqueous layer was extracted three times with ethyl acetate
- washThe combined organic layers were washed with sat NaHCO3 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-f5b78fb38d1c45b3b62efda05b70320a
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06906067B2
Reaction notes
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