Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

Base Information

• Chemical Name: Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester
• CAS No.: 594836-40-5
• Molecular Formula: C₂₄H₃₁NO₄S₂
• Molecular Weight: 461.646
• Mol file: 594836-40-5.mol

Synonyms:Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

Chemical Property of Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

There total 4 articles about Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester 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%

cyclohexylmagnesiumchloride (931-51-1) + (2S,3aR,8aS)-3-(mesitylsulfonyl)-3,3a,8,8a-tetrahydroindeno[1,2-d][1,2,3]oxathiazole-2-oxide (446021-62-1) → Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester (594836-40-5)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tet.2005.03.122

Reference yield:

N-((1R,2S)-2-Hydroxy-indan-1-yl)-2,4,6-trimethyl-benzenesulfonamide (175848-32-5) → Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester (594836-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / thionyl chloride; 3,5-lutidine / tetrahydrofuran / -45 °C

2: 90 percent / tetrahydrofuran / -78 °C

With 3,5-Lutidine; thionyl chloride; In tetrahydrofuran;

DOI:10.1016/j.tet.2005.03.122

Reference yield:

(2S,3aR,8aS)-3-(2,4,6-Trimethyl-benzenesulfonyl)-3,3a,8,8a-tetrahydro-1-oxa-2-thia-3-aza-cyclopenta[a]indene 2-oxide (446021-63-2) → Cyclohexanesulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester (594836-40-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / tetrahydrofuran / -20 - 20 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -45 °C

2.2: tetrahydrofuran; hexane / -78 - -75 °C

3.1: 80 percent / thionyl chloride; 3,5-lutidine / tetrahydrofuran / -45 °C

4.1: 90 percent / tetrahydrofuran / -78 °C

With 3,5-Lutidine; thionyl chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2005.03.122

upstream raw materials:

cyclohexylmagnesiumchloride

(2S,3aR,8aS)-3-(mesitylsulfonyl)-3,3a,8,8a-tetrahydroindeno[1,2-d][1,2,3]oxathiazole-2-oxide

N-((1R,2S)-2-Hydroxy-indan-1-yl)-2,4,6-trimethyl-benzenesulfonamide

(2S,3aR,8aS)-3-(2,4,6-Trimethyl-benzenesulfonyl)-3,3a,8,8a-tetrahydro-1-oxa-2-thia-3-aza-cyclopenta[a]indene 2-oxide

Downstream raw materials:

(2S,3aR,8aS)-3-(2,4,6-Trimethyl-benzenesulfonyl)-3,3a,8,8a-tetrahydro-1-oxa-2-thia-3-aza-cyclopenta[a]indene 2-oxide

N-((1R,2S)-2-Hydroxy-indan-1-yl)-2,4,6-trimethyl-benzenesulfonamide

Refernces

• 1、 Han, Zhengxu,Krishnamurthy, Dhileepkumar,Grover, Paul,Fang, Q. Kevin,Su, Xiping,Wilkinson, H. Scott,Lu, Zhi-Hui,Magiera, Daniel,Senanayake, Chris H.. "Practical and highly stereoselective technology for preparation of enantiopure sulfoxides and sulfinamides utilizing activated and functionally differentiated N-sulfonyl-1,2,3-oxathiazolidine-2-oxide derivatives". . p. 6386 - 6408. Retrieved 2007/10/03.