Trimethylamine → 1-(Naphthalene-1-sulfonyl)-pyrrolidin-3-ylamine

HRID 322486Notes

Reaction equation

HRID 322486 reaction equation
[C:1]1([S:11](Cl)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:15][N:16]([CH3:18])C.C(OC([CH:26]1CC[NH:28][CH2:27]1)=O)(C)(C)C.C([O-])(O)=O.[Na+].FC(F)(F)C(O)=O>C(Cl)Cl.CCOC(C)=O.CO.C(Cl)(Cl)Cl>[C:1]1([S:11]([N:16]2[CH2:18][CH2:26][CH:27]([NH2:28])[CH2:15]2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 1146TrimethylamineHCID 6422Trifluoroacetic acidHCID 665601-Naphthalenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22394392tert-Butyl pyrrolidine-3-carboxylate

Product 1

HCID 572418021-(Naphthalene-1-sulfonyl)-pyrrolidin-3-ylamineYield 23%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of 1-naphthalenesulfonyl chloride (1.0 g, 5.4 mmol) in 50 ml of CH2Cl2 with 2 ml of trimethylamine was added 3-t-butoxycarbonylpyrrolidine (1.5 g, 6.5 mmol) in a portion and the resulting solution was stirred at reflux for 48 h. Reaction mixture was concentrated in vacuo, yielding oily mixture which was partioned between 100 ml of EtOAc and NaHCO3 sat'd aqueous solution. Organic layer was separated, dried over Na2SO4 and concentrated in vacuo to provide an oil, which was redissolved in 20 ml of CH2Cl2. Toward this solution was added 1 ml of trifluoroacetic acid and the resulting solution was stirred for 2 h at 25° C. Reaction mixture was concentrated in vacuo, providing a brown oil, which was dissolved in EtOAc and washed with aqueous NaOH. organic layer was concentrated in vacuo to yield an oil which was subjected to column chromatography (30% MeOH/CHCl3) to provide 0.17 g (23%) of the desired product.

Workup

  1. temperatureat reflux for 48 h
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. customyielding oily mixture which
  5. customOrganic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto provide an oil, which
  9. stirringthe resulting solution was stirred for 2 h at 25° C
  10. customReaction mixture
  11. concentrationwas concentrated in vacuo
  12. customproviding a brown oil, which
  13. washwashed with aqueous NaOH
  14. concentrationorganic layer was concentrated in vacuo
  15. customto yield an oil which

Sources & evidence

ORD record
ord-babfea74bc6a43e3af053c0b6d2b5277
Source dataset
uspto-grants-2001_04
Patent number
US06211241B1

Reaction notes

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