Pyridine → (2R,5S)-2-t-Butyl-5-cyclopent-1-enyl-5-phenyl-1,3-dioxolan-4-one
Reaction equation
[C:1]([C@H:5]1[O:9][C:8](=[O:10])[C@@:7]([C:17]2(O)[CH2:21][CH2:20][CH2:19][CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.N1C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[C:1]([C@H:5]1[O:9][C:8](=[O:10])[C@:7]([C:17]2[CH2:21][CH2:20][CH2:19][CH:18]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:6]1)([CH3:4])([CH3:2])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Intermediate (1b) (650 mg, 2.1 mmol) was dissolved in 6.8 mL anhydrous THF and the solution was cooled to 0° C. Thionyl chloride (436 μL, 6 mmol) was added dropwise, followed by the addition of pyridine (777 μL, 9.6 mmol). The mixture was stirred at 0° C. for 1 hour. Saturated aqueous ammonium chloride (14 mL) was added and the mixture was stirred for 5 minutes while warming to room temperature. The layers were separated, and the aqueous layer was washed (2×100 mL EtOAc.). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to yield intermediate (1c) as a light yellow oil (540 mg), which was used in the next step without further purification.
Workup
- stirringthe mixture was stirred for 5 minutes
- temperaturewhile warming to room temperature
- customThe layers were separated
- washthe aqueous layer was washed (2×100 mL EtOAc.)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ba2eb85839e94beaacbe5f163a2f58ca
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202891B2
Reaction notes
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