(2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-carboxylate

Base Information

Chemical Name:(2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-carboxylate
CAS No.:1350971-17-3
Molecular Formula:C₁₆H₁₆N₂O₄S
Molecular Weight:332.38
Hs Code.:

Synonyms:(2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-carboxylate

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Chemical Property of (2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-carboxylate

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Technology Process of (2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-carboxylate

There total 3 articles about (2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-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: 74.0%

: 874-84-0,34312-77-1
2-(2-nitroethenyl)thiophene

: 66646-88-6
methyl 2-(benzylideneamino)acetate

: 1350971-17-3
(2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-carboxylate

Guidance literature:: methyl 2-(benzylideneamino)acetate; With copper(I) trifluoromethanesolfonate toluene complex; N-benzyl-N-((1S,2R)-2-((4-bromophenyl)thio)-1,2-diphenylethyl)-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine; triethylamine; In chloroform; toluene; at 0 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

2-(2-nitroethenyl)thiophene; In chloroform; toluene; at 0 ℃; for 12h; stereoselective reaction; Schlenk technique; Inert atmosphere;
DOI:10.1002/chem.201705301

Reference yield:

: C₁₆H₁₆N₂O₄S

: 1350971-17-3
(2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-carboxylate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 23 ℃; for 5h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ja2100356

Reference yield:

: 34312-77-1
1-(2-thienyl)-2-nitroethene

: 66646-88-6
methyl 2-(benzylideneamino)acetate

: 1350971-17-3
(2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(thiophen-2-yl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: (22α)-21,22-dihydroxy-2,3-dimethoxy-21,22-dihydrostrychnidin-10-one; copper (I) acetate / dichloromethane / -15 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 5 h / 23 °C / Inert atmosphere

With (22α)-21,22-dihydroxy-2,3-dimethoxy-21,22-dihydrostrychnidin-10-one; copper (I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 2: Mannich reaction;
DOI:10.1021/ja2100356