Pyridine → (2R,5S)-2-t-Butyl-5-cyclopent-1-enyl-5-phenyl-1,3-dioxolan-4-one

HRID 218038Notes

Reaction equation

HRID 218038 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

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 11695185(2R,5S)-2-t-Butyl-5-(1-hydroxycyclopentyl)-5-phenyl-1,3-dioxolan-4-one

Product 1

HCID 67242157(2R,5S)-2-t-Butyl-5-cyclopent-1-enyl-5-phenyl-1,3-dioxolan-4-oneYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. stirringthe mixture was stirred for 5 minutes
  2. temperaturewhile warming to room temperature
  3. customThe layers were separated
  4. washthe aqueous layer was washed (2×100 mL EtOAc.)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a3975e91fd8349c8849a4160a9bbdda6
Source dataset
uspto-grants-2012_06
Patent number
US08198304B2

Reaction notes

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