(S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLIC ACID ETHYL ESTER synthesis
- Product Name:(S)-(-)-1-ETHYL-2-PYRROLIDINECARBOXYLIC ACID ETHYL ESTER
- CAS Number:938-54-5
- Molecular formula:C9H17NO2
- Molecular Weight:171.24
Yield: 48%
Reaction Conditions:
with potassium carbonate in dichloromethane;water
Steps:
1.E Ethyl (-)-(S)-1-ethyl-2-pyrrolidinecarboxylate
1E. 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° C. 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. Distillation of the crude product under reduced pressure gave 6.2 g (48% yield from L-proline) of a colourless liquid (bp 26°-27° C./0.6 mm Hg), with 99.8% purity according to GLC.
References:
Astra Lakemedel Aktiebolag US5300660, 1994, A
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