Hydrochloric Acid → HCID 66818280, compound

HRID 1754929Notes

Reaction equation

HRID 1754929 reaction equation
Cl.[Br:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:12][C@H:13]1[CH2:17][O:16]C(C)(C)[O:14]1>O1CCCC1>[Br:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:12][C@H:13]([OH:14])[CH2:17][OH:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66818299HCID 66818299, compound

Product 1

HCID 66818280HCID 66818280, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2 N aqueous HCl solution (15 ml) was added to a solution of the above mixture (4-bromo-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-indole) in tetrahydrofuran (30 ml), and the mixture was stirred at room temperature for eight hours. The reaction mixture was concentrated, and the residue was then diluted with AcOEt. This organic layer was sequentially washed with water (×2) and a saturated aqueous NaCl solution, and then dried and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (CH2Cl2-MeOH) to give (S)-3-(4-bromo-indol-1-yl)-propane-1,2-diol as a colorless solid (2.05 g, 95%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was then diluted with AcOEt
  3. washThis organic layer was sequentially washed with water (×2)
  4. dry with materiala saturated aqueous NaCl solution, and then dried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-bf65f47c7c55462d9285652b51128508
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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