Water → HCID 24984813, compound

HRID 503955Notes

Reaction equation

HRID 503955 reaction equation
[Li].C[O:3][C:4](=O)[CH2:5][N:6]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:27])[CH2:7]1.O>C1COCC1>[F:26][C:22]1[CH:21]=[C:20]([S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH:8]3[CH2:9][CH2:10][N:6]([CH2:5][CH2:4][OH:3])[CH2:7]3)=[C:12]([CH3:27])[CH:13]=2)(=[O:19])=[O:18])[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3028194LithiumHCID 59428402HCID 59428402, compound

Product 1

HCID 24984813HCID 24984813, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium alluminiumhydride (1.0 M in THF, 0.51 mL) was added to a solution of {3-[4-(3-fluoro-benzenesulfonyl)-2-methyl-phenyl]-pyrrolidin-1-yl}-acetic acid methyl ester (100 mg, 0.2554 mmol) in THF (1 mL) and the resulting mixture was stirred at room temperature for 1 hour. Water was slowly added and the mixture was extracted with DCM. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (DCM/MeOH/NH4OH) to give 7 mg of 2-{3-[4-(3-fluoro-benzenesulfonyl)-2-methyl-phenyl]-pyrrolidin-1-yl}-ethanol, MS (M+H)=364.

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting crude material was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-a6471e24420149069d468db8f44ff63e
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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