Pyrrolidine → trans-1,2,3,4-Tetrahydro-2-hydroxy-1-(pyrrolidin-1-yl)naphthalene

HRID 1651606

Reaction equation

HRID 1651606 reaction equation
[O:1]1[CH:3]2[CH2:4][CH2:5][C:6]3[C:11]([CH:2]12)=[CH:10][CH:9]=[CH:8][CH:7]=3.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)C>[OH:1][C@@H:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C@H:2]1[N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 921821,2-Epoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 14476580trans-1,2,3,4-Tetrahydro-2-hydroxy-1-(pyrrolidin-1-yl)naphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2-epoxy-1,2,3,4-tetrahydronaphthalene (19.8 g), pyrrolidine (15 ml) and ethanol (75 ml) was stirred at reflux for 2 hours and evaporated of the volatiles under reduced pressure. The residue was dissolved in ether and the solution was extracted with IN hydrochloric acid (200 ml). The acid extract was washed with ether and basified with 1N sodium hydroxide aqueous solution with cooling. The mixture was extracted with ether (2X) and the combined ether extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The residual viscous liquid was distilled under vacuum to yield trans-1,2,3,4-tetrahydro-2-hydroxy-1-(pyrrolidin-1-yl)naphthalene (16.5 g), b.p. 128°-135°/0.25 torr.

Workup

  1. temperatureat reflux for 2 hours
  2. customevaporated of the volatiles under reduced pressure
  3. dissolutionThe residue was dissolved in ether
  4. extractionthe solution was extracted with IN hydrochloric acid (200 ml)
  5. extractionThe acid extract
  6. washwas washed with ether and basified with 1N sodium hydroxide aqueous solution
  7. temperaturewith cooling
  8. extractionThe mixture was extracted with ether (2X)
  9. washthe combined ether extracts were washed with water
  10. dry with materialdried over magnesium sulfate
  11. customevaporated under reduced pressure
  12. distillationThe residual viscous liquid was distilled under vacuum

Sources & evidence

ORD record
ord-f664f57207a94bad851ab6c6ace6b5f5
Source dataset
uspto-grants-1990_05
Patent number
US04929627

Linked notes

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