Benzenesulfonic Acid → HCID 68902973, compound

HRID 2110355Notes

Reaction equation

HRID 2110355 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 68902973HCID 68902973, compoundYield 84.9%

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 (350 mg, 1.12 mmol) was dissolved in methanol (20 mL) and benzenesulfonic acid (17 mg, 0.11 mmol) was added. The mixture was stirred for 6 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 260 mg (82%) of (2S,3S)-3-(1H-indol-1-yl)-3-thien-2-ylpropane-1,2-diol. HRMS: calcd for C15H15NO2S+H+, 274.08963; found (ESI, [M+H]+), 274.0892.

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-8e6b6dcc5bd3492d8e5eae45cf661d18
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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