Dicyclohexylcarbodiimide → (S)-Benzyl 2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

HRID 64834

Reaction equation

HRID 64834 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C1CC[CH:32]([N:35]=[C:36]=NC2CCCCC2)CC1.O1CCCC1.CNC>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]([N:35]([CH3:36])[CH3:32])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 101987Benzyloxycarbonyl-L-prolineHCID 22320367Dimethylamine tetrahydrofuran

Product 1

HCID 13564352(S)-Benzyl 2-(dimethylcarbamoyl)pyrrolidine-1-carboxylateYield 88.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 80 ml of dry THF were dissolved 4.9 g (20 m mol) of N-benzyloxycarbonyl-L-proline (29) and 3.5 g (26 m mole) of HOBT and then 4.53 g (22 m mol) of DCC was slowly added to the solution at 0° C. After stirring the mixture for 30 minutes at the same temperature, 10 ml of solution of 2M dimethylamine tetrahydrofuran was added. The resulting mixture was allowed to stand for 12 hours at room temperature. THF was distilled off from the reaction mixture under reduced pressure, the residue thus formed was dissolved in 200 ml of ethyl acetate, and the solution was washed, in succesion, with 75 ml of an aqueous solution of 0.5N hydrochloric acid, 75 ml of a saturated aqueous sodium hydrogencarbonate solution, and 50 ml of water. After drying the organic layer with anhydrous magnesium sulfate, ethyl acetate was distilled off and the residue thus formed was purified by silica gel column chromatography (400 ml of Wako gel C-200, ethyl acetate) to provide 4.8 g of (S)-1-benzyloxycarbonyl-N,N-dimethyl-2-pyrrolidinecarboxamide (88) having a melting point of 66°-67° C.

Workup

  1. additionwas added
  2. distillationTHF was distilled off from the reaction mixture under reduced pressure
  3. customthe residue thus formed
  4. washthe solution was washed, in succesion, with 75 ml of an aqueous solution of 0.5N hydrochloric acid, 75 ml of a saturated aqueous sodium hydrogencarbonate solution, and 50 ml of water
  5. dry with materialAfter drying the organic layer with anhydrous magnesium sulfate, ethyl acetate
  6. distillationwas distilled off
  7. customthe residue thus formed
  8. customwas purified by silica gel column chromatography (400 ml of Wako gel C-200, ethyl acetate)

Sources & evidence

ORD record
ord-d08a818d4e2b43e490d8bab746e57ec4
Source dataset
uspto-grants-1986_09
Patent number
US04610821

Linked notes

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