Methyl iodide → Cyclopentanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:17][O:15][C:14]([C:9]1([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:16]Participants
5
Procedure
In a 150 mL round-bottomed flask 1-tert-butoxycarbonylamino-cyclopentanecarboxylic acid (1.00 g, 4.36 mmol) was dissolved in acetone (30 mL). Potassium carbonate (1.51 g, 10.9 mmol) was added followed by iodomethane (0.41 mL, 6.54 mmol). The reaction mixture was heated at reflux overnight then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between diethyl ether and H2O. The aqueous layer was extracted with diethyl ether. The combined organics were washed with H2O and brine then dried over Na2SO4, filtered and concentrated to afford 1.1 g (99%) of 1-tert-butoxycarbonylamino-cyclopentanecarboxylic acid methyl ester as a white solid.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux overnight
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was partitioned between diethyl ether and H2O
- extractionThe aqueous layer was extracted with diethyl ether
- washThe combined organics were washed with H2O and brine
- dry with materialthen dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-366ca9d6b75d486e8101e7b83085db1e
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329699B2
Reaction notes
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