Hexane → tert-Butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
Reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CCCCCC.C([C@H]1C[O:17][C:16]([CH3:20])([CH3:19])[N:15]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH3:19][C:16]1([CH3:20])[N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:2]([CH:3]=[CH2:4])[CH2:1][O:17]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of methyl triphenylphosphonium bromide (5.63 g, 15.8 mmol) in tetrahydrofuran (140 mL) was added 2.5 M n-butyllithium in hexane (7.35 mL, 18.4 mmol). The deep red solution was stirred at 0° C. for 1 h. Then a solution of tert-butyl (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (from Aldrich, 3.01 g, 13.1 mmol) in tetrahydrofuran (7.3 mL) was added drop wise at 0° C. The red solution was warmed to room temperature and stirred for 12 h. Hexanes was added to the reaction mixture in 4:1 (v/v) ratio. The suspension was filtered through Celite and the filtrate concentrated. The resultant residue was purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give the desired compound as colorless oil (1.92 g, 64%).
Workup
- temperatureThe red solution was warmed to room temperature
- stirringstirred for 12 h
- filtrationThe suspension was filtered through Celite
- concentrationthe filtrate concentrated
- customThe resultant residue was purified by flash chromatography (eluting with 10% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-42654979ffcd44c492a680fc23067aae
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181271B2
Reaction notes
Loading…