Triethylamine → (R)-Pyrrolidine-1,2-dicarboxylic acid 2-tert-butyl ester 1-ethyl ester

HRID 1690638Notes

Reaction equation

HRID 1690638 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl>[CH2:24]([O:23][C:21]([N:9]1[CH2:10][CH2:11][CH2:12][C@@H:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 6931635H-D-Pro-otbu

Product 1

HCID 66902636(R)-Pyrrolidine-1,2-dicarboxylic acid 2-tert-butyl ester 1-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(R)-Pyrrolidine-2-carboxylic acid tert-butyl ester (16.11 g, 94.1 mmol) in DCM (250 ml) under an inert atmosphere of argon is treated with triethyl amine (26 ml, 188 mmol) and then cooled to 0° C. with a ice bath. To this cooled solution is added dropwise ethyl chloroformate (8.99 ml, 94.1 mmol) and the reaction mixture is left to stir at 0° C. for 3 hours. The reaction mixture is washed with 1M HCl (2×100 ml), water, brine, dried over MgSO4 and concentrated in vacuo to yield the titled compound as a clear oil.

Workup

  1. waitthe reaction mixture is left
  2. washThe reaction mixture is washed with 1M HCl (2×100 ml), water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e251b8f6e29141f88cdf18d173c408e0
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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