Sodium hydride → HCID 68577361, compound
Reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]([C:28]#[N:29])([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:15][CH:14]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[H-].[Na+]>COCCOC>[CH3:12][O:11][C:9]([CH:8]1[CH2:7][C:6]([C:28]#[N:29])([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][CH:14]=2)[CH2:5][CH2:4][C:3]1=[O:2])=[O:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 4-cyano-4-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-heptanedioic acid dimethyl ester (8.8 g, 21.1 mmol) in 1,2-dimethoxyethane (176 mL) was charged portions of NaH (60% dispersion, 2.55 g, 63.4 mmol). The reaction mixture was heated to reflux. After 4.5 hr, the ¾ of solvent were evaporated and the mixture cooled to 20° C. with an ice bath and quenched with water (100 mL), HCl 1N (100 mL). The aqueous layer was extracted with ether (100 mL). After basification with NaOH the aqueous phases were extracted with dichloromethane. The combined organics were washed with water, dried over Na2SO4, filtered and concentrated to provide 5-cyano-2-oxo-5-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-cyclohexane-carboxylic acid methyl ester (6.6 g, 81%) as an oil.
Workup
- temperatureThe reaction mixture was heated to reflux
- customthe ¾ of solvent were evaporated
- customquenched with water (100 mL), HCl 1N (100 mL)
- extractionThe aqueous layer was extracted with ether (100 mL)
- extractionAfter basification with NaOH the aqueous phases were extracted with dichloromethane
- washThe combined organics were washed with water
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cbaf757d40684d87aed9973cf5bed2b6
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456164B2
Reaction notes
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