Ethyl 2-(diphenylmethyleneamino)acetate → Ethyl alpha-amino-3-methyl-5-oxopyrrolidine-2-pentanoate

Participants

Reaction Conditions

Reaction Steps

A solution of N-(diphenylmethylene)glycine ethyl ester (Aldrich, 37 mmol) in THF (20 mL) is added to -72° C. solution of sodium bis(trimethylsilylamide) (35 mmol, 0.5M in THF), while the solution is kept below -65° C. The resulting solution is then stirred at -72° C. for 30 min.; followed by the rapid addition of a cooled solution (-72° C.) of the product from EXAMPLE 236 (24 mmol) in THF via canula. The cooling bath is removed immediately and the mixture allowed to warm to 0° C. for 4 h. The reaction mixture is partitioned between ether and 10% aqueous sodium bisulfate, then dried and concentrated. The product is purified by column chromatography. This intermediate is then treated with 0.1N aqueous hydrochloric acid for 3 h, followed by extraction with ether and lyophilization of the aqueous solution, to yield the title material.

Provenance & Evidence