(S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one

Base Information

• Chemical Name: (S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one
• CAS No.: 943587-56-2
• Molecular Formula: C₁₈H₁₉BrN₂O₃
• Molecular Weight: 391.264
• Mol file: 943587-56-2.mol

Synonyms:(S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one

Chemical Property of (S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one

There total 4 articles about (S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-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:

1-(2,4-dimethoxybenzyl)-2-vinylaziridine (848645-61-4) + 5-bromo-1H-pyrrole-2-carboxylic acid methyl ester (934-07-6) → (S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one (943587-56-2) + C18H19BrN2O3

Guidance literature:

With (R,R)-trans-cyclohexanediamine-based phosphine ligand; bis(η3-allyl-μ-chloropalladium(II)); In dichloromethane; at 20 ℃; for 16h; Title compound not separated from byproducts.;

DOI:10.1021/ol070742y

Reference yield:

C20H23BrN2O6 → (S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one (943587-56-2) + C18H19BrN2O3

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; O,O'-[(R)-(1,1'-binaphthyl-2,2'-diphenolyl)]-N-[(R)-2-methyl-1,2,3,4-tetrahydroquinolinyl]phosphoramidite; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 50 ℃; for 65h; Overall yield = 89 %; enantioselective reaction;

DOI:10.1021/acscatal.6b01585

Reference yield:

1-(2,4-dimethoxybenzyl)-2-vinylaziridine (848645-61-4) + 5-bromo-1H-pyrrole-2-carboxylic acid methyl ester (934-07-6) → (S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one (943587-56-2) + C19H23BrN2O4

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In dichloromethane; at 20 ℃; for 16h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja1071509

upstream raw materials:

1-(2,4-dimethoxybenzyl)-2-vinylaziridine

5-bromo-1H-pyrrole-2-carboxylic acid methyl ester

Downstream raw materials:

(S)-6-bromo-2-(2,4-dimethoxybenzyl)-4-(2-hydroxyethyl)-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one