(2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)pyrrolidine

Base Information

Chemical Name:(2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)pyrrolidine
CAS No.:214072-16-9
Molecular Formula:C₃₀H₃₉NO₅
Molecular Weight:493.643
Hs Code.:

Synonyms:(2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)pyrrolidine

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Chemical Property of (2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)pyrrolidine

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Technology Process of (2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)pyrrolidine

There total 11 articles about (2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)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: 96.0%

: 214072-15-8
(2R,5R)-1-[(Benzyloxy)carbonyl]-5-butyl-2-(4-hydroxy-7-benzoyloxyheptyl)pyrrolidine

: 214072-16-9
(2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)pyrrolidine

Guidance literature:: With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 30h;
DOI:10.1016/S0040-4020(98)00498-0

Reference yield:

: 54313-25-6
4-penten-1-yllithium

: 214072-16-9
(2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)pyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1.1: 79.5 percent / CuBr_.DMS / BF_3.Et₂O / diethyl ether / -78 °C / heating to 20 deg C during 4-5 h

2.1: 73.6 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 18 h / -5 °C

3.1: 96 percent / Et₃N / 3 h / 20 °C

4.1: 75 percent / CuI / diethyl ether / 36 h / -20 °C

5.1: 69 percent / phosphate buffer; m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C / pH 8

6.1: 88 percent / CuI / tetrahydrofuran / 2 h / -20 °C

7.1: BH_3.SMe₂ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

7.2: 82 percent / H₂O₂; NaOH / ethanol; tetrahydrofuran; diethyl ether / 0 °C / additional heating at reflux for 1 h

8.1: 72 percent / Pyridine / CH₂Cl₂ / 3 h / -40 °C

9.1: 96 percent / Pyridinium dichromate / CH₂Cl₂ / 30 h / 20 °C

With pyridine; sodium tetrahydroborate; copper(l) iodide; dipyridinium dichromate; phosphate buffer; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Substitution / 2.1: Reduction / 3.1: Tosylation / 4.1: Substitution / 5.1: Epoxidation / 6.1: Condensation / 7.1: Reduction / 7.2: water addition / 8.1: Acylation / 9.1: Oxidation;
DOI:10.1016/S0040-4020(98)00498-0

Reference yield:

: 5211-23-4
N-carbobenzyloxy-L-proline methyl ester

: 214072-16-9
(2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4-hydroxo-7-benzoyloxyheptyl)pyrrolidine

Guidance literature:: Multi-step reaction with 10 steps

1.1: 75 percent / tetraethylammonium p-toluenesulfonate / -5 °C / Electrolysis; GC-monitoring

2.1: 79.5 percent / CuBr_.DMS / BF_3.Et₂O / diethyl ether / -78 °C / heating to 20 deg C during 4-5 h

3.1: 73.6 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 18 h / -5 °C

4.1: 96 percent / Et₃N / 3 h / 20 °C

5.1: 75 percent / CuI / diethyl ether / 36 h / -20 °C

6.1: 69 percent / phosphate buffer; m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C / pH 8

7.1: 88 percent / CuI / tetrahydrofuran / 2 h / -20 °C

8.1: BH_3.SMe₂ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

8.2: 82 percent / H₂O₂; NaOH / ethanol; tetrahydrofuran; diethyl ether / 0 °C / additional heating at reflux for 1 h

9.1: 72 percent / Pyridine / CH₂Cl₂ / 3 h / -40 °C

10.1: 96 percent / Pyridinium dichromate / CH₂Cl₂ / 30 h / 20 °C

With pyridine; sodium tetrahydroborate; copper(l) iodide; dipyridinium dichromate; phosphate buffer; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; tetraethylammonium tosylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Methoxylation / 2.1: Substitution / 3.1: Reduction / 4.1: Tosylation / 5.1: Substitution / 6.1: Epoxidation / 7.1: Condensation / 8.1: Reduction / 8.2: water addition / 9.1: Acylation / 10.1: Oxidation;
DOI:10.1016/S0040-4020(98)00498-0