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

Base Information

• Chemical Name: methyl (2S)-2-{(3R,4R)-4-[(1E)-but-1-enyl]-4-methyl-1-(4-methylbenzenesulfonyl)pyrrolidin-3-yl}but-3-enoate
• CAS No.: 705962-77-2
• Molecular Formula: C₂₁H₂₉NO₄S
• Molecular Weight: 391.532

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

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

Chemical Property:

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

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

(E)-2-methylpenta-2,4-dien-1-ol (1572-71-0) → methyl (2S)-2-{(3R,4R)-4-[(1E)-but-1-enyl]-4-methyl-1-(4-methylbenzenesulfonyl)pyrrolidin-3-yl}but-3-enoate (705962-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 74 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C

2.1: (S)-MeO-MOP; Ni(acac)2 / tetrahydrofuran; hexane / 62 h / 4 °C / 760 Torr

2.2: 88 percent / diethyl ether

With bis(acetylacetonate)nickel(II); di-isopropyl azodicarboxylate; (S)-MEO-MOP; triphenylphosphine; In tetrahydrofuran; hexane;

DOI:10.1021/ja049506y

Reference yield:

(E)-4-methyl-N-(penta-2,4-dien-1-yl)benzenesulfonamide (136573-40-5) → methyl (2S)-2-{(3R,4R)-4-[(1E)-but-1-enyl]-4-methyl-1-(4-methylbenzenesulfonyl)pyrrolidin-3-yl}but-3-enoate (705962-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 74 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 20 °C

2.1: (S)-MeO-MOP; Ni(acac)2 / tetrahydrofuran; hexane / 62 h / 4 °C / 760 Torr

2.2: 88 percent / diethyl ether

With bis(acetylacetonate)nickel(II); di-isopropyl azodicarboxylate; (S)-MEO-MOP; triphenylphosphine; In tetrahydrofuran; hexane;

DOI:10.1021/ja049506y

Reference yield:

methyl (2S)-2-{(3R,4R)-4-[(1E)-but-1-enyl]-4-methyl-1-(4-methylbenzenesulfonyl)pyrrolidin-3-yl}but-3-enoate (705962-77-2) → (S)-2-[(3R,4R)-4-((E)-But-1-enyl)-4-methyl-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

upstream raw materials:

(E)-2-methylpenta-2,4-dien-1-ol

(E)-4-methyl-N-(penta-2,4-dien-1-yl)benzenesulfonamide

Downstream raw materials:

(3R,4R)-3-((E)-But-1-enyl)-4-((S)-1-methoxymethyl-allyl)-3-methyl-1-(toluene-4-sulfonyl)-pyrrolidine

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