Hydrochloric Acid → HCID 53856410, compound

HRID 1358483Notes

Reaction equation

HRID 1358483 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH2:4][O:3]1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[N:9]1([CH2:8][CH2:7][C@H:5]([OH:6])[CH2:4][OH:3])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 56992103HCID 56992103, compound

Product 1

HCID 53856410HCID 53856410, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 1-[2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1H-indole (520 mg, 2.12 mmol) in THF (10 ml) was added portionwise 1N-HCl (8.48 ml). After the addition was completed, the reaction mixture was stirred at room temperature for 2.5 hours. An aqueous solution of NaHCO3 was added, and the resulting mixture was stirred for several minutes. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate) and concentrated in vacuo to give (S)-4-(1-indolyl)-butane-1,2-diol (449.3 mg, 103%) as an oil. This material was used immediately without further purification. To an ice cooled solution of (S)-4-(1-indolyl)-butane-1,2-diol in DMF (10 ml) was added imidazole (433 mg, 6.36 mmol) followed by tert-butyldimethylsilylchloride (335 mg, 2.23 mmol). After 30 minutes, the ice-bath was removed and then the mixture was stirred overnight at room temperature. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo. The residue was purified by silica gel (15 g) column chromatography eluting with hexane/ethyl acetate (20:1) to give (S)-[1-(tert-butyldimethylsilyloxy)-4-(1-indolyl)]-butan-2-ol (542 mg, 80.0%) as a colorless oil.

Workup

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred for several minutes
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-deda211559cd4b04ba19a8c609035904
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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