Acetyl chloride → (S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate

HRID 1416634Notes

Reaction equation

HRID 1416634 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:19](Cl)(=O)C>CO>[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([O:15][CH3:19])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 688168(S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 12.5 g (47.4 mmol) sample of CBZ-L-proline (Aldrich) was dissolved in 250 mL of methanol and 1.7 mL of acetyl chloride was added. The reaction mixture was stirred at room temperature for 16 hours. The solvents were removed, the residue was dissolved in CHCl3, and this solution was washed with NaHCO3 solution, dried, filtered and concentrated. The residue was purified on a silica gel column, eluting with 1:1 ethyl acetate:hexane to give 14 g of the title compound.

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in CHCl3
  3. washthis solution was washed with NaHCO3 solution
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column
  8. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-0cd0132809354663b84cdbf3dff4c39e
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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