Hydrochloric Acid → 5-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine

HRID 611066Notes

Reaction equation

HRID 611066 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([CH:15](O)[CH2:16][O:17][Si](C(C)(C)C)(C)C)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[O:17][CH:16]=[CH:15][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 537375441-Benzyl-3-(2-tert-butyldimethylsiloxy-1-hydroxyethyl)-4-piperidinone

Product 1

HCID 183773045-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 3.055 g (8.403 mmol) of 1-benzyl-3-(2-tert-butyldimethylsiloxy-1-hydroxyethyl)-4-piperidinone was dissolved in 100 ml of methanol, 10 ml of concentrated hydrochloric acid was added, followed by stirring at room temperature for 10 minutes. The solvent was distilled off under reduced pressure with heating. The resulting residue was dissolved in water. After this solution was alkalified with aqueous sodium hydroxide, it was extracted with dichloromethane 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=9/1 to 6/1) to yield 5-benzyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. temperaturewith heating
  3. dissolutionThe resulting residue was dissolved in water
  4. extractionwas extracted with dichloromethane 3 times
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 6/1)

Sources & evidence

ORD record
ord-7408190c491b47eb8fdda0630025edf9
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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