Sodium hydride → tert-butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:16][CH2:17][C:18]#[N:19])[C:9]([CH3:15])([C:11]([O:13]C)=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(Cl)Cl.CCO>O1CCOCC1>[C:18]([C:17]1[CH2:16][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:9]([CH3:10])([CH3:15])[C:11]=1[OH:13])#[N:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
45 g of methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate were dissolved in dioxane (240 ml) under nitrogen and 7.9 g of sodium hydride were added. The mixture was refluxed for 6 hours (120° C. internal temperature), and then left to stand overnight at room temperature (TLC: CH2Cl2/EtOH 90/10). The solvent was evaporated, water was added (1000 ml) and the mixture was brought to pH 3-4 with citric acid. The aqueous layer was extracted 4 times with ethyl acetate, the extracts washed with a limited amount of water and evaporated. Then the residue was taken up with hexane, evaporated and crystallized from hexane. 33.1 g of tert-butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate were thus obtained (yield: 85%).
Workup
- waitleft
- customThe solvent was evaporated
- additionwater was added (1000 ml)
- extractionThe aqueous layer was extracted 4 times with ethyl acetate
- washthe extracts washed with a limited amount of water
- customevaporated
- customevaporated
- customcrystallized from hexane
Sources & evidence
- ORD record
- ord-43aa7d612b35400289a99addeac945c7
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481585B2
Reaction notes
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