Hydrochloric Acid → HCID 54274472, compound

HRID 611403Notes

Reaction equation

HRID 611403 reaction equation
[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[CH:2]1.B.Cl>O1CCCC1>[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[CH:21]=[CH:20][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 19600260HCID 19600260, compound

Product 1

HCID 54274472HCID 54274472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 19.040 g (61.953 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-ylsulfonyl)benzoic acid in 100 ml of tetrahydrofuran, 74.3 ml (74.3 mmol) of 1.0 M borane in tetrahydrofuran was added dropwise under ice-cooling, followed by overnight stirring at room temperature. Dilute hydrochloric acid was added, followed by stirring at room temperature for 0.5 hours and 3 extractions with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The residue was dissolved in 50 ml of methanol; 15 ml of concentrated hydrochloric acid was added, followed by stirring at 70° C. for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to yield the desired product.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. stirringby stirring at room temperature for 0.5 hours
  4. extraction3 extractions with ethyl acetate
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in 50 ml of methanol
  8. addition15 ml of concentrated hydrochloric acid was added
  9. stirringby stirring at 70° C. for 1 hour
  10. additionThe reaction mixture was poured into water
  11. extractionextracted with ethyl acetate 3 times
  12. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  13. distillationthe solvent was distilled off under reduced pressure
  14. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-edca7b6143644ca194cad7ff38d39a8e
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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