3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol

Base Information

Chemical Name:3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol
CAS No.:870246-65-4
Molecular Formula:C₂₀H₃₅NO₄SSi
Molecular Weight:413.654
Hs Code.:

Synonyms:3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol

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Chemical Property of 3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol

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Technology Process of 3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol

There total 8 articles about 3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol 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: 94.0%

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

: 870246-65-4
3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1016/j.tetlet.2005.09.024

Reference yield:

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

: 870246-65-4
3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 7 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

7: 94 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

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

Reference yield:

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

: 870246-65-4
3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

2: 94 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

With lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1016/j.tetlet.2005.09.024