Benzenesulfonic Acid → HCID 68906941, compound

HRID 2110358Notes

Reaction equation

HRID 2110358 reaction equation
CC1(C)[O:6][C@@H:5]([C@@H:7]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[CH2:4][O:3]1.C1(S(O)(=O)=O)C=CC=CC=1>CO.C(OCC)(=O)C>[N:8]1([C@@H:7]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[C@H:5]([OH:6])[CH2:4][OH:3])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

5

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 68904626HCID 68904626, compound

Product 1

HCID 68906941HCID 68906941, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[(S )-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](2-thienyl)methyl]-1H-indole (160 mg, 0.51 mmol) was dissolved in methanol (10 mL) and benzenesulfonic acid (10 mg, 0.06 mmol) was added. The mixture was stirred for 16 hours then diluted with ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate, water, and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via flash column chromatography (silica, 5% methanol/chloroform) to afford 102 mg (74%) of (2S,3R)-3-(1H-indol-1-yl)-3-thien-2-ylpropane-1,2-diol that was carried directly to the next step.

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate, water, and saturated brine
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified via flash column chromatography (silica, 5% methanol/chloroform)

Sources & evidence

ORD record
ord-0d6db5c6a2d9499fbcfb9d46bd66274a
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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