Benzoyl chloride → methyl 1-benzoylpyrrolidine-2-carboxylate

HRID 352209Notes

Reaction equation

HRID 352209 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:11][O:12][C:13](=[O:19])[C@@H:14]1[CH2:18][CH2:17][CH2:16][NH:15]1.CCN(CC)CC>C(Cl)Cl>[CH3:11][O:12][C:13]([CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:19]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 338198methyl 1-benzoylpyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (1.40 mL, 12.1 mmol) was added in a dropwise manner to a mixture of L-proline methyl ester hydrochloride (2.00 g, 12.1 mmol) and Et3N (4.20 mL, 30.2 mmol) in CH2Cl2 (40 mL) and the resulting mixture stirred overnight at rt. The mixture was concentrated in vacuo and the residue treated with water and extracted with EtOAc and the combined extracts dried over Na2SO4. Concentration left a residue which was loaded onto a silica gel column and eluted with MeOH/CH2Cl2 which allowed for isolation of 2.76 g (94%) of the title compound as a white solid. MS(ES): (M+1)+ 234.2 m/z.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue treated with water
  3. extractionextracted with EtOAc
  4. dry with materialthe combined extracts dried over Na2SO4
  5. concentrationConcentration
  6. waitleft a residue which
  7. washeluted with MeOH/CH2Cl2 which

Sources & evidence

ORD record
ord-8a012de93b184e2b935ed3e0cf816508
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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