{(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester

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Chemical Name:{(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester
CAS No.:433711-83-2
Molecular Formula:C₂₇H₄₂N₂O₅
Molecular Weight:474.641
Hs Code.:

Synonyms:{(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester

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Chemical Property of {(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester

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Technology Process of {(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester

There total 14 articles about {(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl 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: 91.0%

: 6524-17-0,29283-76-9,6386-72-7
(Z)-1-propenyllithium

: 335693-89-5
{(2S)-methoxy-(1R)-[1'-(4-methoxybenzyl)-5'-oxo-2',5'-dihydro-1H-pyrrol-(2'R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester

: 433711-83-2
{(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester

Guidance literature:: (Z)-1-propenyllithium; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;

{(2S)-methoxy-(1R)-[1'-(4-methoxybenzyl)-5'-oxo-2',5'-dihydro-1H-pyrrol-(2'R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; chloro-trimethyl-silane; In tetrahydrofuran; diethyl ether; at -78 - -20 ℃; for 1h; Further stages.;
DOI:10.1021/ja0126226

Reference yield:

: 176108-62-6
(R)-4-but-3-enoyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 433711-83-2
{(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 99 percent / H₂ / Pd/C / methanol / 14 h / 20 °C / atmospheric pressure

2.1: 92 percent / tetrahydrofuran / -78 - 20 °C

3.1: 99 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 20 °C

4.1: 90 percent / p-TsOH; methanol / 0.5 h / 20 °C

5.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 2 h / 20 °C

6.1: 90 percent / MgSO₄ / CH₂Cl₂ / 4 h / 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: H₂ / Lindlar's catalyst / ethyl acetate / 20 °C / atmospheric pressure

9.1: 62 mg / Mo(CO)6 / acetonitrile; H₂O / Heating

10.1: CuBr*Me₂S / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

10.2: 91 percent / TMSCl; DMPU / tetrahydrofuran; diethyl ether / 1 h / -78 - -20 °C

With methanol; n-butyllithium; copper(I) bromide dimethylsulfide complex; hexacarbonyl molybdenum; pyridine-SO₃ complex; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 5.1: Parikh-Doering oxidation;
DOI:10.1021/ja0126226

Reference yield:

: 335693-75-9
(1S,2S)-(1-formyl-2-methoxy-2-methylpentyl)-carbamic acid tert-butyl ester

: 433711-83-2
{(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / MgSO₄ / CH₂Cl₂ / 4 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C

3.1: H₂ / Lindlar's catalyst / ethyl acetate / 20 °C / atmospheric pressure

4.1: 62 mg / Mo(CO)6 / acetonitrile; H₂O / Heating

5.1: CuBr*Me₂S / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

5.2: 91 percent / TMSCl; DMPU / tetrahydrofuran; diethyl ether / 1 h / -78 - -20 °C

With n-butyllithium; copper(I) bromide dimethylsulfide complex; hexacarbonyl molybdenum; hydrogen; magnesium sulfate; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1021/ja0126226