(2R,2′R,S_S)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine

Base Information

• Chemical Name: (2R,2′R,S_S)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine
• CAS No.: 1597449-89-2
• Molecular Formula: C₂₁H₃₂N₂O₃S
• Molecular Weight: 392.563

Synonyms:(2R,2′R,S_S)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine

Chemical Property of (2R,2′R,S_S)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine

Chemical Property:

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Technology Process of (2R,2′R,S_S)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine

There total 4 articles about (2R,2′R,S_S)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine 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%

(R)-(N-benzyloxycarbonyl)-2-(2-oxoethyl)pyrrolidine (1036404-01-9) + allyl bromide (106-95-6) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (2R,2′R,SS)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine (1597449-89-2)

Guidance literature:

(R)-(N-benzyloxycarbonyl)-2-(2-oxoethyl)pyrrolidine; (S)-2-methylpropane-2-sulfinamide; With titanium(IV) tetraethanolate; indium; In tetrahydrofuran; at 23 ℃; for 1h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; at 60 ℃; for 5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo500446f

Reference yield:

(4R,RS)-N-(tert-butylsulfinyl)-7-bromohept-1-en-4-amine (1597449-87-0) → (2R,2′R,SS)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine (1597449-89-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

2.1: hydrogenchloride / tetrahydrofuran; water / 2 h / 0 - 23 °C / Inert atmosphere

2.2: 0.08 h / 0 °C / Inert atmosphere

2.3: 3 h / 23 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / water; 1,4-dioxane; tert-butyl alcohol / 1.5 h / 23 °C

4.1: indium; titanium(IV) tetraethanolate / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere

4.2: 5 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; hydrogenchloride; titanium(IV) tetraethanolate; indium; sodium periodate; osmium(VIII) oxide; potassium hexamethylsilazane; In tetrahydrofuran; 1,4-dioxane; water; tert-butyl alcohol;

DOI:10.1021/jo500446f

Reference yield:

(2R,Rs)-2-allyl-(N-tert-butylsulfinyl)pyrrolidine (1597449-88-1) → (2R,2′R,SS)-(N-benzyloxycarbonyl)-2-[2′-(tert-butylsulfinamine)-4′-pentenyl]pyrrolidine (1597449-89-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / tetrahydrofuran; water / 2 h / 0 - 23 °C / Inert atmosphere

1.2: 0.08 h / 0 °C / Inert atmosphere

1.3: 3 h / 23 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / water; 1,4-dioxane; tert-butyl alcohol / 1.5 h / 23 °C

3.1: indium; titanium(IV) tetraethanolate / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere

3.2: 5 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; hydrogenchloride; titanium(IV) tetraethanolate; indium; sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; water; tert-butyl alcohol;

DOI:10.1021/jo500446f

upstream raw materials:

(R)-(N-benzyloxycarbonyl)-2-(2-oxoethyl)pyrrolidine

allyl bromide

(S)-2-methylpropane-2-sulfinamide

(4R,R_S)-N-(tert-butylsulfinyl)-7-bromohept-1-en-4-amine

Downstream raw materials:

(2R,2′R,S_S)-(N-benzyloxycarbonyl)-2-[(2′-tert-butylsulfinamine)-4′-heptenyl]pyrrolidine

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