Hydrochloric Acid → HCID 11068249, compound

HRID 324622Notes

Reaction equation

HRID 324622 reaction equation
[CH2:1]([C:4]1[C:5]([OH:21])=[C:6]([Br:20])[CH:7]=[C:8]2[C:12]=1[C@H:11]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:2]=C.[O:22]=[O+][O-].[BH4-].[Na+].Cl>CO>[Br:20][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([CH2:1][CH2:2][OH:22])[C:5]=1[OH:21])[C@H:11]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:10][CH2:9]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 10861106HCID 10861106, compound

Product 1

HCID 11068249HCID 11068249, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-N-[2-(7-allyl-5-bromo-6-hydroxyindan-1-yl)ethyl]propionamide (588 mg, 1.67 mmol.) in methanol (30 mL) was cooled to about −70° C., to which was introduced ozone for 5 minutes. After confirming the disappearance of the starting material, an excess amount of powdery sodium borohydride (510 mg, 13.4 mmol.) was added to reaction mixture at about −70° C. to decompose ozonide. The reaction mixture was warmed to room temperature, which was neutralized with dilute hydrochloric acid, followed by extracting the organic matter with a mixture of ethyl acetate:butanol=1:1. The extract solution was dried over anhydrous magnesium sulfate, from which the solvent was distilled off under reduced pressure. The residue was then washed with diethyl ether to afford the title compound (yield 0.59 g, 99%).

Workup

  1. extractionby extracting the organic matter
  2. additionwith a mixture of ethyl acetate
  3. dry with materialThe extract solution was dried over anhydrous magnesium sulfate, from which the solvent
  4. distillationwas distilled off under reduced pressure
  5. washThe residue was then washed with diethyl ether

Sources & evidence

ORD record
ord-75346678b8e54726aa47cecd5e175864
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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