5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:441794-84-9
Molecular Formula:C₂₆H₃₉NO₆
Molecular Weight:461.599
Hs Code.:

5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of 5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of 5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

There total 14 articles about 5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)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: 87.0%

: 67-64-1
acetone

: 441794-83-8
3S-isopropyl-2R-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

: 441794-84-9
5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/jo011184i

Reference yield:

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

: 441794-84-9
5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; n-butyllithium; copper bromide dimethyl sulfide complex; [bis(acetoxy)iodo]benzene; 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

Reference yield:

: 108963-96-8
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

: 441794-84-9
5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 100 percent / LiHMDS / tetrahydrofuran / 4 h / -78 °C

2: 70 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

3: DIBAl-H / tetrahydrofuran / 2 h / -78 °C

4: 11.4 g / pTSA

5: 46 percent / CuBr₂*Me₂S; BF₃*Et₂O; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

6: 81 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 20 °C

7: 90 percent / H₂ / Pd/C / ethyl acetate / 24 h / 2068.65 Torr

8: 88 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

9: 68 percent / LiCl; Hunig's base / acetonitrile

10: 90 percent / H₂ / Pd/C / ethyl acetate

11: 88 percent / NaBH₄ / methanol

12: 75 percent / TEMPO; PhI(OAc)2 / CH₂Cl₂ / 6 h

13: 87 percent / LiHMDS / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; n-butyllithium; copper bromide dimethyl sulfide complex; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile; 9: Horner-Emmons-Wadsworth reaction;
DOI:10.1021/jo011184i