1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[3-[(4-methoxyphenyl) methoxy]-1-methylenepropyl]-5-oxo-, 1,1-dimethylethyl ester, (2S,3R)-

Base Information

Chemical Name:1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[3-[(4-methoxyphenyl) methoxy]-1-methylenepropyl]-5-oxo-, 1,1-dimethylethyl ester, (2S,3R)-
CAS No.:874454-29-2
Molecular Formula:C28H45NO6Si
Molecular Weight:519.754
Hs Code.:

1-Pyrrolidinecarboxylic acid,
2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[3-[(4-methoxyphenyl)
methoxy]-1-methylenepropyl]-5-oxo-, 1,1-dimethylethyl ester, (2S,3R)-

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Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[3-[(4-methoxyphenyl) methoxy]-1-methylenepropyl]-5-oxo-, 1,1-dimethylethyl ester, (2S,3R)-

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Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[3-[(4-methoxyphenyl) methoxy]-1-methylenepropyl]-5-oxo-, 1,1-dimethylethyl ester, (2S,3R)-

There total 2 articles about 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[3-[(4-methoxyphenyl) methoxy]-1-methylenepropyl]-5-oxo-, 1,1-dimethylethyl ester, (2S,3R)- 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: 86.0%

: 1-((3-bromobut-3-enyloxy)methyl)-4-methoxybenzene

: 81658-27-7
(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: 874454-29-2
(4R,5S)-1-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)-4-(4-(4-methoxybenzyloxy)but-1-en-2-yl)pyrrolidin-2-one

Guidance literature:: 1-((3-bromobut-3-enyloxy)methyl)-4-methoxybenzene; With tert.-butyl lithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

In tetrahydrofuran; hexane; at -78 - -50 ℃; for 0.0833333h;

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate; With chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -50 ℃; for 1h;
DOI:10.1021/jm0508336

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 874454-29-2
(4R,5S)-1-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)-4-(4-(4-methoxybenzyloxy)but-1-en-2-yl)pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 77 percent / La(OTf)3 / toluene / 0.08 h

2.1: t-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: CuCN / tetrahydrofuran; hexane / 0.08 h / -78 - -50 °C

2.3: 86 percent / TMSCl / tetrahydrofuran; hexane / 1 h / -50 °C

With tert.-butyl lithium; lanthanum(lll) triflate; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jm0508336

Reference yield:

: 874454-29-2
(4R,5S)-1-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)-4-(4-(4-methoxybenzyloxy)but-1-en-2-yl)pyrrolidin-2-one

: 874454-33-8
(4R,5S)-1-tert-butoxycarbonyl-5-(tert-butyldimethylsilyloxymethyl)-4-(4-(phenylsulfonyloxy)but-1-en-2-yl)pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / aq. DDQ / CH₂Cl₂ / 1 h / 20 °C

2: 92 percent / N,N-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 4 h / 0 - 20 °C

With dmap; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1021/jm0508336