Methyl iodide → 1-(tert-Butyl) 2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.[Cl-].[Na+].O>[CH3:17][O:15][C:14]([CH:9]1[CH:10]([OH:13])[CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution containing 3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (60, 16 g, 71 mmol. See: Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2005, 45, 15923) in DMF (100 mL) was cooled to 0° C. To this solution was added K2CO3 (16 g, 116 mmol) followed by iodomethane (5.4 mL, 87 mmol). The reaction mixture was slowly warmed to ambient temperature over 1 h at which time it became a yellow heterogeneous solution. This mixture was heated at 90° C. for 1 h and then cooled to ambient temperature. The solution was diluted with brine, extracted with diethyl ether, dried over anhydrous Na2SO4, filtered, and concentrated to afford 14.8 g (87%) of 3-hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (61) as a yellow oil (See: Demange, L.; Cluzeau, J.; Menez, A.; Dugave, C. Tetrahedron Lett. 2001, 42, 651).
Workup
- temperatureThis mixture was heated at 90° C. for 1 h
- temperaturecooled to ambient temperature
- extractionextracted with diethyl ether
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a6c7aded37ca439fabef994796351368
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415486B2
Reaction notes
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