Reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([N:7]([CH2:15][CH:16]=[O:17])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH2:6].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].N12CCC(CC1)CC2>CO>[C:10]([O:9][C:8]([N:7]([C@@H:4]([CH:5]=[CH2:6])[CH2:3][O:2][CH3:1])[CH2:15][CH:16]([OH:17])[C:19](=[CH2:20])[C:18]([O:22][CH3:23])=[O:21])=[O:14])([CH3:12])([CH3:13])[CH3:11]Participants
Procedure
To a solution of (S)-tert-butyl 1-methoxybut-3-en-2-yl(2-oxoethyl)carbamate (Intermediate 252, 1.475 g, 6.06 mmol) and methyl acrylate (0.82 ml, 9.09 mmol) in MeOH (0.2 ml) under nitrogen at room temperature was added quinuclidine (0.337 g, 3.03 mmol). The reaction mixture was stirred at that temperature overnight. Another 100 mg of quinuclidine was added and the reaction was stirred for another 24 hours. The reaction mixture was then partitioned between water and ethyl acetate. The layers were separated and the organics were washed with water and brine, then dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-30% ethyl acetate/hexanes) afforded the title compound as a clear oil (1.28 g, 65%). The product is a mixture of two diastereomers.
Workup
- stirringthe reaction was stirred for another 24 hours
- customThe reaction mixture was then partitioned between water and ethyl acetate
- customThe layers were separated
- washthe organics were washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e080e644243f4d5097cb3905e31e5222
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309245B2
Linked notes
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