(2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:441794-86-1
Molecular Formula:C₂₆H₃₉NO₅
Molecular Weight:445.599
Hs Code.:

Synonyms:(2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 21 articles about (2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic 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: 90.0%

: 441794-85-0
5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

: 441794-86-1
(2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate;
DOI:10.1021/jo011184i

Reference yield: 31.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1200341-48-5
(1'S,2R,3S,3'S,5S)-5-(3-butylcarbamoyl-1-hydroxy-4-methyl-pentyl)-3-isopropyl-2-(4-methoxyphenyl)-pyrrolidine-1-sulfonic acid 2,2,2-trichloro-ethyl ester

: 441794-86-1
(2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 441794-87-2
(1'S,2R,3S,3'S,5S)-5-(3-butylcarbamoyl-1-hydroxy-4-methyl-pentyl)-3-isopropyl-2-(4-methoxyphenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: (1'S,2R,3S,3'S,5S)-5-(3-butylcarbamoyl-1-hydroxy-4-methyl-pentyl)-3-isopropyl-2-(4-methoxyphenyl)-pyrrolidine-1-sulfonic acid 2,2,2-trichloro-ethyl ester; With zinc copper; acetic acid; In methanol; at 20 ℃; for 16h; Inert atmosphere;

With hydrogenchloride; In methanol; at 0 - 20 ℃; for 24h; Inert atmosphere;

di-tert-butyl dicarbonate; With tetrabutylammomium bromide; potassium carbonate; In dichloromethane; water; at 0 - 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo5015195

Reference yield:

: 104-92-7
1-bromo-4-methoxy-benzene

: 441794-86-1
(2R,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 46 percent / CuBr₂*Me₂S; BF₃*Et₂O; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

2: 81 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 20 °C

3: 90 percent / H₂ / Pd/C / ethyl acetate / 24 h / 2068.65 Torr

4: 88 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

5: 68 percent / LiCl; Hunig's base / acetonitrile

6: 90 percent / H₂ / Pd/C / ethyl acetate

7: 88 percent / NaBH₄ / methanol

8: 75 percent / TEMPO; PhI(OAc)2 / CH₂Cl₂ / 6 h

9: 87 percent / LiHMDS / tetrahydrofuran / 1 h / -78 °C

10: 80 percent / PCl₅ / CH₂Cl₂ / 0.5 h / -60 °C

11: 90 percent / H₂ / Pd/C / ethyl acetate

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; n-butyllithium; copper bromide dimethyl sulfide complex; [bis(acetoxy)iodo]benzene; phosphorus pentachloride; boron trifluoride diethyl etherate; hydrogen; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile; 5: Horner-Emmons-Wadsworth reaction;
DOI:10.1021/jo011184i