(2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine

Base Information

Chemical Name:(2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine
CAS No.:104795-12-2
Molecular Formula:C₂₁H₃₅NO₄Si
Molecular Weight:393.599
Hs Code.:

Synonyms:

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Chemical Property of (2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine

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Technology Process of (2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine

There total 6 articles about (2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine 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:

: 114358-14-4
O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate

: 104795-12-2
(2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: H₂ / Pd/C / methanol / 1 h / 20 °C

2.1: 30 percent H₂O₂; SeO₂ / acetone / 0.67 h / 10 - 15 °C

3.1: 960 mg / NaOH / methanol; H₂O / 1 h / 20 °C

4.1: 69 percent / H₂O₂; Et₄NCl; K₂CO₃ / Na₂WO₄*2H₂O / CH₂Cl₂; H₂O

5.1: n-BuLi / hexane / 0.5 h / 0 °C

5.2: 45 percent / hexane; CH₂Cl₂ / 0.5 h / 0 °C

6.1: H₂; AcOH / Pd/C / methanol / 11 h / 0 - 20 °C

7.1: 1.43 g / NaHCO₃ / ethyl acetate; tetrahydrofuran / 0.5 h / 20 °C

With sodium hydroxide; n-butyllithium; selenium(IV) oxide; tetraethylammonium chloride; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; potassium carbonate; acetic acid; sodium tungstate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetone; 1.1: Catalytic hydrogenation / 2.1: Oxidation / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Metallation / 5.2: Substitution / 6.1: Catalytic hydrogenation / 7.1: Substitution;
DOI:10.1246/bcsj.72.2737

Reference yield:

: (4R)-4-(t-butyldimethylsilyloxy)-2-[3-(t-butyldimethylsilyloxy)-1-propynyl]-1-hydroxypyrrolidine

: 104795-12-2
(2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / HCl / methanol; H₂O / 5 h / 0 °C

2: H₂; AcOH / Pd/C / methanol / 11 h / 0 - 20 °C

3: 1.43 g / NaHCO₃ / ethyl acetate; tetrahydrofuran / 0.5 h / 20 °C

With hydrogenchloride; hydrogen; sodium hydrogencarbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; 1: Hydrolysis / 2: Catalytic hydrogenation / 3: Substitution;
DOI:10.1246/bcsj.72.2737

Reference yield:

: 159330-31-1
(R)-3-[(1,1-dimethylethyl)dimethylsilyloxy]-pyrrolidine

: 104795-12-2
(2R,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(3-hydroxypropyl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 9 percent / H₂O₂; Et₄NCl / Na₂WO₄*2H₂O / CH₂Cl₂; H₂O / 4 h / 0 °C

2.1: n-BuLi / hexane / 0.5 h / 0 °C

2.2: 45 percent / hexane; CH₂Cl₂ / 0.5 h / 0 °C

3.1: H₂; AcOH / Pd/C / methanol / 11 h / 0 - 20 °C

4.1: 1.43 g / NaHCO₃ / ethyl acetate; tetrahydrofuran / 0.5 h / 20 °C

With n-butyllithium; tetraethylammonium chloride; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; acetic acid; sodium tungstate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; 1.1: Oxidation / 2.1: Metallation / 2.2: Substitution / 3.1: Catalytic hydrogenation / 4.1: Substitution;
DOI:10.1246/bcsj.72.2737