(2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate

Base Information

• Chemical Name: (2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate
• CAS No.: 74397-33-4
• Molecular Formula: C₁₈H₁₇NO₅S
• Molecular Weight: 359.403
• Mol file: 74397-33-4.mol

Synonyms:(2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate

Chemical Property of (2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate

There total 3 articles about (2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate 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: 84.0%

(+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione (152903-44-1) + methanesulfonyl chloride (124-63-0) → (2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate (74397-33-4)

Guidance literature:

In pyridine; 1.) 0 deg C, 3 h; 2.) 0 deg C, overnight;

DOI:10.1021/jo01308a012

Reference yield:

(R)-2-amino-3-phenylpropanol (5267-64-1) → (2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate (74397-33-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / 140 °C

2: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

With triethylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2005.04.011

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → (2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate (74397-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaBH₄; I₂ / tetrahydrofuran / Heating

1.2: MeOH

2.1: 96 percent / 140 °C

3.1: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

With sodium tetrahydroborate; iodine; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2005.04.011

upstream raw materials:

(+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione

methanesulfonyl chloride

(R)-2-amino-3-phenylpropanol

D-(R)-phenylalanine

Downstream raw materials:

(+)-(R)-2-(1-benzyl-2-bromoethyl)-1H-isoindole-1,3(2H)-dione

(+)-(R)-2-(1-benzyl-2-iodoethyl)-1H-isoindole-1,3(2H)-dione

S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate