Hydrochloric Acid → 1-Benzenesulfonyl-2-vinylpyrrolidine

HRID 660653Notes

Reaction equation

HRID 660653 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([S:17]([N:20]2[CH2:24][CH2:23][CH2:22][CH:21]2[CH:25]=O)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:11]1([S:17]([N:20]2[CH2:24][CH2:23][CH2:22][CH:21]2[CH:25]=[CH2:1])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3251421Potassium bis(trimethylsilyl)amideHCID 144249041-Benzenesulfonylpyrrolidine-2-carbaldehyde

Product 1

HCID 688399341-Benzenesulfonyl-2-vinylpyrrolidine

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a suspension of methyl triphenylphosphonium bromide (357 mg, 1 mmol) in THF (10 mL) at −78° C. is added dropwise KHMDS (1 mmol, 2 mL of 0.5M solution). To this yellow solution is added dropwise a solution of 1-benzenesulfonylpyrrolidine-2-carbaldehyde (235 mg, 1 mmol) in THF (1 mL). The mixture is stirred at −78° C. for 2 h then is allowed to warm to RT. The mixture is poured into 1N HCl and extracted with EtOAc. The organic phase is washed with brine and dried over magnesium sulfate then the solvent removed under reduced pressure. The resulting oil is purified by flash chromatography using a gradient of 0-20% EtOAc/hexane as eluent to give the title compound.

Workup

  1. temperatureto warm to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe resulting oil is purified by flash chromatography

Sources & evidence

ORD record
ord-7bdd69c47f18465dbe44e7ebe1773e6f
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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