Potassium tert-butoxide → (S)-tert-butyl 4-(1-cyclopropylvinyl)-2,2-dimethyloxazolidine-3-carboxylate
Reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH:7]1([C:10]([C@H:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O)[CH2:9][CH2:8]1>CCOCC.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:7]1([C:10]([C@H:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH2:1])[CH2:9][CH2:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
To a suspension of potassium tert-butoxide (9.29 g, 82.80 mmol) in ether (250 mL) at room temperature was added methyltriphenylphosphonium bromide (29.6 g, 82.80 mmol). The mixture turned bright yellow and was heated to 40° C. for 1 hour. The mixture was cooled to room temperature and a solution of (R)-tert-butyl 4-(cyclopropanecarbonyl)-2,2-dimethyloxazolidine-3-carboxylate (Intermediate 231, 11.15 g, 41.40 mmol) in ether (30 mL) was added and the reaction mixture was stirred for 2 hours. The reaction was quenched with water (10 mL) and the layers were separated. The aqueous was extracted once with ether. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-15% ethyl acetate/hexanes) afforded the title compound as a colorless oil (9.84 g, 89%).
Workup
- temperatureThe mixture was cooled to room temperature
- customThe reaction was quenched with water (10 mL)
- customthe layers were separated
- extractionThe aqueous was extracted once with ether
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fe83ffc1e1f14c449de4c09114f90389
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309245B2
Reaction notes
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