tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate
CAS No.:194932-22-4
Molecular Formula:C₁₈H₃₅NO₃Si
Molecular Weight:341.566
Hs Code.:

Synonyms:tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate

There total 1 articles about tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-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:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 194932-22-4
tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 20 °C / Large scale

1.2: 0 - 20 °C / Large scale

2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

3.1: magnesium / diethyl ether / 30 °C / Reflux

3.2: 4 h / 0 - 20 °C

4.1: triethylamine / toluene / 0.17 h / -78 °C

4.2: 3.5 h / -78 °C

With 1H-imidazole; magnesium; triethylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 194932-22-4
tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate

: 149396-15-6
(2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-[N-(p-toluenesulfonyl)azetidin-3-yl]pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 36 percent / t-BuOOH; SeO₂ / CH₂Cl₂ / 20 h / 20 °C

2.1: pyridinium p-toluenesulfonate / CH₂Cl₂

2.2: 9-BBN; Na₂BO₄ / tetrahydrofuran

4.1: Et₃N; MsCl / tetrahydrofuran / 0.67 h / 4 °C

4.2: 77 percent / NaH / dimethylformamide / 4 h / 20 °C

With tert.-butylhydroperoxide; selenium(IV) oxide; pyridinium p-toluenesulfonate; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Oxidation / 2.1: Etherification / 2.2: Reduction / 4.1: Cyclization / 4.2: Cyclization;
DOI:10.7164/antibiotics.50.567

Reference yield:

: 194932-22-4
tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate

: 4-(tert-butyl-dimethyl-silanyloxy)-2-[1-hydroxymethyl-2-(toluene-4-sulfonylamino)-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 36 percent / t-BuOOH; SeO₂ / CH₂Cl₂ / 20 h / 20 °C

2.1: pyridinium p-toluenesulfonate / CH₂Cl₂

2.2: 9-BBN; Na₂BO₄ / tetrahydrofuran

With tert.-butylhydroperoxide; selenium(IV) oxide; pyridinium p-toluenesulfonate; In dichloromethane; 1.1: Oxidation / 2.1: Etherification / 2.2: Reduction;
DOI:10.7164/antibiotics.50.567