Iodoethane → benzyl (S)-N-ethylpyrrolidine-2-carboxylate

HRID 927987

Reaction equation

HRID 927987 reaction equation
I[CH2:2][CH3:3].[NH:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:2]([N:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH3:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 736155Benzyl L-prolinate

Product 1

HCID 10421496benzyl (S)-N-ethylpyrrolidine-2-carboxylateYield 56.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Iodoethane (1.34 g) was added to a mixture of benzyl (S)-pyrrolidine-2-carboxylate (1.0 g) and potassium carbonate (1.77 g) in dry DMF (7 mL) and the resultant mixture was stirred at room temperature for 3 days. The mixture was diluted with water, extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane with a gradient of 10-20% to give benzyl (S)—N-ethylpyrrolidine-2-carboxylate (0.643 g) as a pale straw coloured oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and pentane with a gradient of 10-20%

Sources & evidence

ORD record
ord-b0c189607e2846e6931b6cd459974696
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Linked notes

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