Pyrrolidine → HCID 22475095, compound

HRID 2103140Notes

Reaction equation

HRID 2103140 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[O:13][C:12]2[CH:14]=[C:15]([F:22])[C:16]([S:18](Cl)(=[O:20])=[O:19])=[CH:17][C:11]=2[O:10]1.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>C(OCC)C.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[O:13][C:12]2[CH:14]=[C:15]([F:22])[C:16]([S:18]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)(=[O:20])=[O:19])=[CH:17][C:11]=2[O:10]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 22475115HCID 22475115, compound

Product 1

HCID 22475095HCID 22475095, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,2-bis-(2,4-difluoro-phenyl)-6-fluoro-benzo[1,3]dioxole-5-sulfonyl chloride (250 mg, 0.54 mmol) in diethylether (3 mL) was added pyrrolidine (0.11 mL, 1.35 mmol, 2.5 eq.). The reaction mixture was diluted with ethyl acetate (50 mL), washed with an aqueous solution of hydrochloric acid (IN), brine and water. The organic layer was dried over sodium sulfate and the volatiles were removed in vacuo. Purification by flash chromatography afforded the title compound (198 mg, 74%) as a white foam.

Workup

  1. washwashed with an aqueous solution of hydrochloric acid (IN), brine and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe volatiles were removed in vacuo
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-ba11af06803e49e49cbedd96d619f58b
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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