(3S,4R)-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoro-2-oxo-1-[(S)-1-phenylethyl]pyrrolidine

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Chemical Name:(3S,4R)-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoro-2-oxo-1-[(S)-1-phenylethyl]pyrrolidine
CAS No.:215999-30-7
Molecular Formula:C₂₀H₂₇FN₂O₃
Molecular Weight:362.444
Hs Code.:

Synonyms:(3S,4R)-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoro-2-oxo-1-[(S)-1-phenylethyl]pyrrolidine

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Chemical Property of (3S,4R)-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoro-2-oxo-1-[(S)-1-phenylethyl]pyrrolidine

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Technology Process of (3S,4R)-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoro-2-oxo-1-[(S)-1-phenylethyl]pyrrolidine

There total 3 articles about (3S,4R)-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoro-2-oxo-1-[(S)-1-phenylethyl]pyrrolidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

: 75-65-0
tert-butyl alcohol

: 190954-43-9
ethyl 1-{(3S,4S)-4-fluoro-5-oxo-1-[(S)-1-phenylethyl]pyrrolidin-3-yl}cyclopropanecarboxylate

: 215999-30-7
(3S,4R)-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoro-2-oxo-1-[(S)-1-phenylethyl]pyrrolidine

Guidance literature:: ethyl 1-{(3S,4S)-4-fluoro-5-oxo-1-[(S)-1-phenylethyl]pyrrolidin-3-yl}cyclopropanecarboxylate; With sodium hydroxide; water; In ethanol; at 40 ℃; for 6h;

With diphenyl-phosphinic acid; triethylamine; In toluene; for 2h; Heating;

tert-butyl alcohol; In toluene; for 21h; Heating;
DOI:10.3987/COM-03-9972

Reference yield:

: 190954-37-1
ethyl 1-{(3S)-4,4-difluoro-5-oxo-1-[(S)-1-phenylethyl]pyrrolidin-3-yl}cyclopropanecarboxylate

: 215999-30-7
(3S,4R)-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoro-2-oxo-1-[(S)-1-phenylethyl]pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 10.2 g / aq. NaOH / ethanol / 6 h / 40 °C

2: 3.30 g / Et₃N; diphenylphosphoryl azide / toluene / 2 h / Heating

With sodium hydroxide; diphenylphosphoranyl azide; triethylamine; In ethanol; toluene; 2: Curtius rearrangement;
DOI:10.1021/jm020328y