(1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate

Base Information

Chemical Name:(1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate
CAS No.:1282523-32-3
Molecular Formula:C₂₁H₂₀N₂O₅
Molecular Weight:380.4
Hs Code.:

Synonyms:(1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate

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Chemical Property of (1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate

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Technology Process of (1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate

There total 5 articles about (1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-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: 92.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1456887-56-1
(1R,2S,3R)-2-nitro-3-phenylspiro[cyclopropane-1,3'-indolin]-2'-one

: 1282523-32-3
(1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 0.25h;
DOI:10.1039/c3cc45369c

Reference yield:

: 563-70-2
bromonitromethane

: C₂₀H₁₉NO₃

: tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate

: 1282523-32-3
(1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate

Guidance literature:: bromonitromethane; With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((2S,4S,8R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)thiourea; In tert-butyl methyl ether; for 0.0833333h;

C₂₀H₁₉NO₃; With sodium carbonate; In tert-butyl methyl ether; at 20 ℃; for 72h; optical yield given as %ee; enantioselective reaction;
DOI:10.1002/chem.201003423

Reference yield:

: 68235-96-1
rac-3-chloroindolin-2-one

: 1282523-32-3
(1S,2S,3R)-tert-butyl 3-nitro-2'-oxo-2-phenylspiro[cyclopropane-1,3'-indoline]-1'-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 1-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-3-phenylthiourea / toluene / 2 h / 20 °C

2: sodium formate / dimethyl sulfoxide / 12 h / 20 °C

3: dmap / dichloromethane / 0.25 h / 20 °C

With dmap; 1-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-3-phenylthiourea; sodium formate; In dichloromethane; dimethyl sulfoxide; toluene; 1: |Michael Addition;
DOI:10.1039/c3cc45369c