Ethanol → 114812-34-9

HRID 1463517Notes

Reaction equation

HRID 1463517 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([NH2:8])=[O:7].[CH2:9](O)[CH3:10].C(N(CC)CC)C.C(Br)C>C1(C)C=CC=CC=1>[CH2:9]([N:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([NH2:8])=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 6332Ethyl BromideHCID 8471TriethylamineHCID 111306L-Prolinamide

Product 1

HCID 10866443114812-34-9

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (S)-2-pyrrolidine carboxamide (13.2 g, 116 mmol) in ethanol (140 ml) K2CO3 (17.6 g, 128 mmol) and triethylamine (1.2 ml, 8.6 mmol) were added. The mixture was heated to 30 C. and stirred vigorously. Then ethylbromide (10.4 ml, 138 mmol) were added during 0.5 hours. After 30 hours the mixture was diluted with toluene (50 ml) and washed with water (50 ml). The organic layer was concentrated at reduced pressure. The residue was dissolved in toluene (150 ml) and washed with a small amount of aqueous sodium hydroxide, dried with magnesium sulfate, and evaporated to dryness in vacuo. Yield 10.7 g (65%).

Workup

  1. temperatureThe mixture was heated to 30 C
  2. washwashed with water (50 ml)
  3. concentrationThe organic layer was concentrated at reduced pressure
  4. dissolutionThe residue was dissolved in toluene (150 ml)
  5. washwashed with a small amount of aqueous sodium hydroxide
  6. dry with materialdried with magnesium sulfate
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-1faed03adb3f45bebd879e17cfc1840d
Source dataset
uspto-grants-1994_04
Patent number
US05300660

Reaction notes

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