methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate

Base Information

Chemical Name:methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate
CAS No.:705962-68-1
Molecular Formula:C₂₁H₂₉NO₄S
Molecular Weight:391.532
Hs Code.:

Synonyms:methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate

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Chemical Property of methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate

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Technology Process of methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate

There total 1 articles about methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate 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:

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 124-38-9,18923-20-1
carbon dioxide

: 557-20-0
diethylzinc

: 463304-99-6
4-methyl-N,N-di-[(2E)-penta-2,4-dienyl]benzenesulfonamide

: methyl (2S)-2-[(3S,4R)-4-(prop-2-enyl)-1-(4-methylbenzenesulfonyl)pyrrolidin-3-yl]but-3-enoate

: methyl (2R)-2-[(3R,4S)-4-(prop-2-ennyl)-1-(4-methylbenzenesulfonyl)pyrrolidin-3-yl]but-3-enoate

: 705962-68-1
methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate

: methyl (2R)-2-{(3R,4S)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate

Guidance literature:: carbon dioxide; diethylzinc; 4-methyl-N,N-di-[(2E)-penta-2,4-dienyl]benzenesulfonamide; With bis(acetylacetonate)nickel(II); (S)-MEO-MOP; In tetrahydrofuran; hexane; at 0 ℃; for 8h; under 760 Torr;

diazomethane; In diethyl ether; Title compound not separated from byproducts;
DOI:10.1021/ja049506y

Reference yield:

: 705962-68-1
methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate

: (S)-2-[(3S,4R)-4-((E)-Pent-1-enyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-but-3-en-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.5h;
DOI:10.1021/ja049506y

Reference yield:

: 705962-68-1
methyl (2S)-2-{(3S,4R)-1-(4-methylbenzenesulfonyl)-4-[(1E)-pent-1-enyl]pyrrolidin-3-yl}but-3-enoate

: (R)-2-[(3S,4R)-4-Hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-methoxy-propan-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

2.1: NaH / tetrahydrofuran; dimethylformamide / 2 h / 20 °C

3.1: O₃ / diethyl ether / 0.25 h / -78 °C

3.2: LiAlH₄ / diethyl ether / -78 - 20 °C

With lithium aluminium tetrahydride; sodium hydride; ozone; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja049506y