(4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

Base Information

Chemical Name:(4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate
CAS No.:906528-97-0
Molecular Formula:C₂₃H₃₂N₂O₃
Molecular Weight:384.519
Hs Code.:

Synonyms:(4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

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Chemical Property of (4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

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Technology Process of (4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

There total 14 articles about (4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-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%

: 906528-98-1
(4R,5R)-tert-butyl 5-ethynyl-2,2-dimethyl-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

: 591-50-4
iodobenzene

: 906528-97-0
(4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

Guidance literature:: With piperidine; bis-triphenylphosphine-palladium(II) chloride; at 70 ℃;
DOI:10.1016/j.bmc.2006.03.048

Reference yield: 82.0%

: 123-75-1
pyrrolidine

: 906528-95-8
((4R,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2-phenylethynyl)oxazolidin-4-yl)methyl 4-methylbenzenesulfonate

: 906528-97-0
(4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

Guidance literature:: In N,N-dimethyl-formamide; at 45 ℃; for 72h;
DOI:10.1016/j.bmc.2006.03.048

Reference yield:

: 95715-87-0
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

: 906528-97-0
(4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi; ZnBr₂ / diethyl ether; hexane / 0 - 20 °C

1.2: 41 percent / diethyl ether; hexane / -78 - 20 °C

2.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3.1: 93 percent / acetic acid / 5 h / 60 °C

4.1: 89 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide / 16 h / 20 °C

5.1: 98 percent / p-TsOH*H₂O / acetone / 6 h / Heating

6.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.25 h / 20 °C

7.1: 99 percent / piperidine / PdCl₂(PPh₃)2 / 70 °C

8.1: 64 percent / pyridine / 35 h / 20 °C

9.1: 82 percent / dimethylformamide / 72 h / 45 °C

With piperidine; pyridine; 1H-imidazole; dmap; n-butyllithium; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; zinc dibromide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; acetone; 7.1: Sonogashira coupling;
DOI:10.1016/j.bmc.2006.03.048