(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester

Base Information

Chemical Name:(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester
CAS No.:148966-79-4
Molecular Formula:C₂₃H₃₀FNO₆S
Molecular Weight:467.559
Hs Code.:

Synonyms:(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester

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Chemical Property of (3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester

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Technology Process of (3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester

There total 18 articles about (3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl 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%

: 188557-38-2
(E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester

: 148966-79-4
(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester

Guidance literature:: (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester; With diethyl methoxy borane; In tetrahydrofuran; methanol; at -78 ℃; for 0.333333h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -78 ℃; for 1.5h;
DOI:10.1021/jo9722156

Reference yield:

: 160204-82-0
(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

: 148966-79-4
(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 81 percent / aq. HF / acetonitrile / 1 h / 20 °C

2.1: Et₂BOMe / tetrahydrofuran; methanol / 0.33 h / -78 °C

2.2: 91 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / -78 °C

With diethyl methoxy borane; hydrogen fluoride; In tetrahydrofuran; methanol; acetonitrile; 1.1: desilylation / 2.1: complexation / 2.2: Reduction;
DOI:10.1021/jo9722156

Reference yield:

: 109721-08-6
(S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester

: 148966-79-4
(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -30 - 2 °C

1.2: 100 percent / tetrahydrofuran; hexane / 0.92 h / -66 - -30 °C

2.1: 74 percent / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 0.92 h / 0 - 15 °C

3.1: 98 percent / methanol / 0.53 h / 0 °C

4.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

4.2: 1.98 g / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 0 °C

5.1: 91 percent / toluene / 1 h / Heating

6.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.2: 62 percent / tetrahydrofuran / 6 h / -78 - 0 °C

7.1: 81 percent / aq. HF / acetonitrile / 1 h / 20 °C

8.1: Et₂BOMe / tetrahydrofuran; methanol / 0.33 h / -78 °C

8.2: 91 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / -78 °C

With n-butyllithium; diethyl methoxy borane; hydrogen fluoride; potassium tert-butylate; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 1.1: Metallation / 1.2: Acylation / 2.1: Cyclization / 3.1: Ring cleavage / 4.1: Metallation / 4.2: Condensation / 5.1: Elimination / 6.1: Metallation / 6.2: mesylation / 7.1: desilylation / 8.1: complexation / 8.2: Reduction;
DOI:10.1021/jo9722156