Benzyl chloroformate → 1-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylate

HRID 2203692Notes

Reaction equation

HRID 2203692 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].C1COCC1.O.[C:23](Cl)(=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CCOCC>[N:2]1([C:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:32])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1

Participants

6

Reactant 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 19261352Methyl pyrrolidine-3-carboxylate hydrochlorideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 113460671-Benzyl 3-methyl pyrrolidine-1,3-dicarboxylateYield 54.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To methyl pyrrolidine-3-carboxylate hydrochloride (4.00 g, 24.15 mmol) and K2CO3 (6.68 g, 48.3 mmol) in 1:1 THF-water (100 mL) was added benzyl carbonochloridate (3.57 mL, 25.36 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. Ether (50 mL) was added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography (hexane:ethyl acetate 3:1) to give 1-benzyl 3-methyl pyrrolidine-1,3-dicarboxylate (3.45 g, 54% yield) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by chromatography (hexane:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-bafc1a126c5a4d07bd4237f7d9a8dc7b
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

Loading…