(2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole

Base Information

• Chemical Name: (2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole
• CAS No.: 920035-12-7
• Molecular Formula: C₂₆H₂₅NO₅S
• Molecular Weight: 463.554
• Mol file: 920035-12-7.mol

Synonyms:(2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole

Chemical Property of (2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole

There total 3 articles about (2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole 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: 63.0%

(2S)-2-benzyloxymethyl-1-(4-methylphenylsulfonyl)pyrrolidin-4-one (905859-13-4) + (3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) → (2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole (920035-12-7)

Guidance literature:

(2S)-2-benzyloxymethyl-1-(4-methylphenylsulfonyl)pyrrolidin-4-one; (3,4-methylenedioxy)phenylmagnesium bromide; In tetrahydrofuran; at -78 - 20 ℃; for 2h;

With boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20 ℃; for 0.25h;

DOI:10.1016/j.tet.2006.10.002

Reference yield:

benzyl bromide (100-39-0) → (2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole (920035-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 20 h / Heating

1.2: 82 percent / Jones reagent / acetone / 0.33 h / 0 °C

2.1: tetrahydrofuran / 2 h / -78 - 20 °C

2.2: 63 percent / BF₃*OEt₂ / tetrahydrofuran / 0.25 h / 0 - 20 °C

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.tet.2006.10.002

Reference yield:

(2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine (261157-02-2) → (2S)-2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)-2,5-dihydro-1H-pyrrole (920035-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 20 h / Heating

1.2: 82 percent / Jones reagent / acetone / 0.33 h / 0 °C

2.1: tetrahydrofuran / 2 h / -78 - 20 °C

2.2: 63 percent / BF₃*OEt₂ / tetrahydrofuran / 0.25 h / 0 - 20 °C

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.tet.2006.10.002

upstream raw materials:

(2S)-2-benzyloxymethyl-1-(4-methylphenylsulfonyl)pyrrolidin-4-one

(3,4-methylenedioxy)phenylmagnesium bromide

benzyl bromide

(2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine

Downstream raw materials:

2-benzyloxymethyl-4-(3,4-dioxymethylenephenyl)-1-(4-methylphenylsulfonyl)pyrrolidin-3-one