(5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one

Base Information

• Chemical Name: (5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one
• CAS No.: 1477797-95-7
• Molecular Formula: C₂₉H₂₉NO₃
• Molecular Weight: 439.554
• Mol file: 1477797-95-7.mol

Synonyms:(5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one

Chemical Property of (5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one

There total 1 articles about (5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one 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: 86.0%

trans-2-pentenoic acid (13991-37-2) + (R)-5-trityloxymethyl-2-pyrrolidinone (124665-91-4) → (5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one (1477797-95-7)

Guidance literature:

(R)-5-trityloxymethyl-2-pyrrolidinone; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

trans-2-pentenoic acid; With pivaloyl chloride; triethylamine; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1055/s-0033-1338974

Reference yield: 85.0%

(5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one (1477797-95-7) + vinyl magnesium bromide (1826-67-1) → (5R)-1-[(3R)-3-ethylpent-4-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one (1477797-96-8)

Guidance literature:

(5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one; vinyl magnesium bromide; With copper(I) bromide dimethylsulfide complex; dimethylsulfide; In tetrahydrofuran; at -45 ℃; for 0.333333h; Inert atmosphere; Molecular sieve;

(5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one; In tetrahydrofuran; at -45 ℃; for 1h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; Inert atmosphere;

DOI:10.1055/s-0033-1338974

Reference yield:

(5R)-1-[(2E)-pent-2-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one (1477797-95-7) → methyl (R)-4-((R)-3-ethylpent-4-enamido)-5-(trityloxy)pentanoate (1477798-07-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(I) bromide dimethylsulfide complex; dimethylsulfide / tetrahydrofuran / 0.33 h / -45 °C / Inert atmosphere; Molecular sieve

1.2: 1 h / -45 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: tetrahydrofuran; hexane / 36 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

With copper(I) bromide dimethylsulfide complex; dimethylsulfide; In tetrahydrofuran; hexane;

DOI:10.1055/s-0033-1338974

upstream raw materials:

trans-2-pentenoic acid

(R)-5-trityloxymethyl-2-pyrrolidinone

Downstream raw materials:

methyl (R)-4-((R)-3-ethylpent-4-enamido)-5-(trityloxy)pentanoate

(5R)-1-[(3R)-3-ethylpent-4-enoyl]-5-[(triphenylmethoxy)methyl]pyrrolidin-2-one