3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester

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Chemical Name:3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester
CAS No.:870246-69-8
Molecular Formula:C₂₂H₃₇NO₅SSi
Molecular Weight:455.691
Hs Code.:

Synonyms:3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester

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Chemical Property of 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester

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Technology Process of 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester

There total 7 articles about 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester 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: 99.0%

: ethyl 3-[(2S,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-acrylate

: 870246-69-8
3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 10h;
DOI:10.1016/j.tetlet.2005.09.024

Reference yield:

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

: 870246-69-8
3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 2.93 g / triethylamine / CH₂Cl₂ / 10 h / 20 °C

2: 3.93 g / imidazole / dimethylformamide / 2 h / 20 °C

3: 3.47 g / NaBH₄; LiCl; MeOH / 12 h / 20 °C

4: 950 mg / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 - 20 °C

5: 1.06 g / CH₂Cl₂ / 5 h / 20 °C

6: 99 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

With 1H-imidazole; methanol; sodium tetrahydroborate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation / 5: Wittig olefination;
DOI:10.1016/j.tetlet.2005.09.024

Reference yield:

: 16257-57-1
methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate

: 870246-69-8
3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 3.93 g / imidazole / dimethylformamide / 2 h / 20 °C

2: 3.47 g / NaBH₄; LiCl; MeOH / 12 h / 20 °C

3: 950 mg / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 - 20 °C

4: 1.06 g / CH₂Cl₂ / 5 h / 20 °C

5: 99 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

With 1H-imidazole; methanol; sodium tetrahydroborate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 3: Swern oxidation / 4: Wittig olefination;
DOI:10.1016/j.tetlet.2005.09.024