(-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate

Base Information

Chemical Name:(-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate
CAS No.:1315128-91-6
Molecular Formula:C₁₉H₂₇NO₄
Molecular Weight:333.428
Hs Code.:

Synonyms:(-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate

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Chemical Property of (-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate

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Technology Process of (-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate

There total 12 articles about (-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate 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: 93.0%

: 1315128-48-3
(+)-ethyl (2Z,6R)-6-[(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

: 1315128-91-6
(-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 0.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201100649

Reference yield:

: 1315128-48-3
(+)-ethyl (2Z,6R)-6-[(tert-butoxycarbonyl)amino]-6-phenylhex-2-enoate

: tert-butyl (2S,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate

: 1315128-91-6
(-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate

Guidance literature:: With caesium carbonate; In tert-butyl alcohol; at 70 ℃; for 3h; optical yield given as %de;
DOI:10.1002/chem.201100649

Reference yield:

: 913344-40-8
tert-butyl N-formyl carbamate

: 1315128-91-6
(-)-tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-phenylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₃₈H₃₄NO₄P; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / tetrahydrofuran / 0.7 h / 20 °C / Inert atmosphere

2: potassium hydroxide / methanol / 1.5 h / 20 °C

3: tetrahydrofuran / 4 h / 50 °C / Inert atmosphere

4: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; 1,4-dioxane; water / 20 °C / Inert atmosphere

5: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₃₈H₃₄NO₄P; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; potassium tert-butylate; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; 4: Suzuki-Miyaura coupling / 5: Aza-Michael addition;
DOI:10.1002/chem.201100649