Butylamine → (S)-1-benzyloxycarbonyl-N-butyl-2-pyrrolidinecarboxamide

HRID 1284987Notes

Reaction equation

HRID 1284987 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[CH2:32]([NH2:36])[CH2:33][CH2:34][CH3:35]>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([NH:36][CH2:32][CH2:33][CH2:34][CH3:35])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8007ButylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 13564336(S)-1-benzyloxycarbonyl-N-butyl-2-pyrrolidinecarboxamideYield 70.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 50 ml of THF was dissolved 4.99 g of N-benzyloxycarbonyl-L-proline and then 2.23 g of triethylamine was added to the solution. Then, after slowly adding thereto 2.39 g of ethyl chloroformate under ice-cooling, the reaction was maintained for one hour at 0° C. to 5° C. Then, 2.19 g of n-butylamine was slowly added to the reaction mixture under ice-cooling, the reaction was further performed for one hour at 0° C. to 5° C. The solvent was removed from the reaction mixture, the residue thus formed was dissolved in ethyl acetate, and the solution was washed successively with an aqueous solution of 1N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution, and a saturated aqueous sodium chloride solution. The organic layer this formed was collected, dried by Glauber's salt, and then concentrated to dryness. The product was recrystallized from water to provide 4.31 g of (S)-1-benzyloxycarbonyl-N-butyl-2-pyrrolidinecarboxamide (30). M. p. 88°-90° C.

Workup

  1. additionThen, after slowly adding
  2. temperaturethe reaction was maintained for one hour at 0° C. to 5° C
  3. temperaturecooling
  4. customThe solvent was removed from the reaction mixture
  5. customthe residue thus formed
  6. washthe solution was washed successively with an aqueous solution of 1N hydrochloric acid
  7. customThe organic layer this formed was collected
  8. dry with materialdried by Glauber's salt
  9. concentrationconcentrated to dryness
  10. customThe product was recrystallized from water

Sources & evidence

ORD record
ord-26789738304b4d388815dbac3b2ade75
Source dataset
uspto-grants-1986_01
Patent number
US04564609

Reaction notes

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