Ethyl Bromide → Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate

HRID 129570Notes

Reaction equation

HRID 129570 reaction equation
Br[CH2:2][CH3:3].[NH:4]1[CH2:11][CH2:10][CH2:9][C@H:5]1[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:18](N(CCOCCOC)CCOCCOC)[CH2:19]OCCOC>ClCCl.O>[CH2:18]([N:4]1[CH2:11][CH2:10][CH2:9][C@H:5]1[C:6]([O:8][CH2:2][CH3:3])=[O:7])[CH3:19]

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 145742L-Proline

Product 1

HCID 10942897Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylateYield 420.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Bromoethane (27.2 g, 0.25 mol) was added during 1 h to a stirred suspension of L-proline (11.5 g, 0.1 mol), potassium carbonate (27.6 g, 0.2 mol), and tris (3,6-dioxaheptyl)amine (TDA-1) (6.5 g, 0.02 mol) in dichloromethane (90 ml) at 25°. The reaction mixture was stirred for another 43 h at 26°-27° C. Water (100 ml ) was added and after stirring for a short while at room temperature, the two homogeneous phases were separated. The waterphase was extracted with another portion of dichloromethane (150 ml). The combined organic phases were dried (MgSO4), filtered, and evaporated affording 14.4 g of a yellow liquid.

Workup

  1. stirringafter stirring for a short while at room temperature
  2. customthe two homogeneous phases were separated
  3. extractionThe waterphase was extracted with another portion of dichloromethane (150 ml)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-2329fbf560034877a33ea498afa3fcae
Source dataset
uspto-grants-1995_11
Patent number
US05468876

Reaction notes

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