Iodoethane → (3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-ethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

29.1 A solution of 150 mg (3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (example 22.4) in 3 ml MeCN and 1 ml THF was treated with 300 mg silver(I) oxide and 0.35 ml iodoethane. The reaction mixture was stirred over night, then was again treated with 300 mg silver(I) oxide and 0.35 ml iodoethane. The reaction mixture was agitated over night at r.t., then filtrated. The filtrate was concentrated. The crude product was purified by chromatography (silica gel; gradient: cyclohexane->EtOAc) to give 90 mg (3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-ethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester as light yellow oil. MS 373.1 ([M−H]−)

Provenance & Evidence