(R_S)-N-benzyl-2-methylpropane-2-sulfinamide

Base Information

• Chemical Name: (R_S)-N-benzyl-2-methylpropane-2-sulfinamide
• CAS No.: 212378-92-2
• Molecular Formula: C₁₁H₁₇NOS
• Molecular Weight: 211.328
• Mol file: 212378-92-2.mol

Synonyms:(R_S)-N-benzyl-2-methylpropane-2-sulfinamide

Chemical Property of (R_S)-N-benzyl-2-methylpropane-2-sulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R_S)-N-benzyl-2-methylpropane-2-sulfinamide

There total 19 articles about (R_S)-N-benzyl-2-methylpropane-2-sulfinamide 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: 92.0%

(R)-N-benzylidene-2-methylpropane-2-sulfinamide (196929-85-8) → (RS)-N-benzyl-2-methylpropane-2-sulfinamide (212378-92-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/ol062633+

Reference yield: 91.0%

benzaldehyde (100-52-7) + (R)-2-methylpropane-2-sulfinamide (196929-78-9) → (RS)-N-benzyl-2-methylpropane-2-sulfinamide (212378-92-2)

Guidance literature:

benzaldehyde; (R)-2-methylpropane-2-sulfinamide; With titanium(IV) tetraethanolate; In tetrahydrofuran; Inert atmosphere; Reflux;

With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2010.09.009

Reference yield: 88.0%

(1S)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl-(R)-2-tert-butylsulfinate + benzylamine (100-46-9) → (RS)-N-benzyl-2-methylpropane-2-sulfinamide (212378-92-2)

Guidance literature:

benzylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

(1S)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl-(R)-2-tert-butylsulfinate; In tetrahydrofuran; at -78 ℃; for 0.166667h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo201825b

upstream raw materials:

(R)-tert-butyl tert-butanethiosulfinate

benzylamine

isopropylmagnesium bromide

(R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide

Downstream raw materials:

(R)-N-benzyl-N-(bis(4-(trifluoromethyl)phenyl)phosphino)-2-methyl-2-propanesulfinamide

(R)-N-benzyl-N-(di-o-tolylphosphino)-2-methyl-2-propanesulfinamide

(R_S)-N-allyl-N-benzyl-2-methylpropane-2-sulfinamide

(2R,2'R,5S)-2-(N-benzyl-S-tert-butylsulfinamidoyl)-3,1,2-oxazaphosphabicyclo[3.3.0]-octane

Refernces

• 1、 Ma, Peng-Ju,Tang, Fan,Yao, Yun,Lu, Chong-Dao. "Addition-Rearrangement of Ketenes with Lithium N- tert-Butanesulfinamides: Enantioselective Synthesis of α,α-Disubstituted α-Hydroxycarboxylic Acid Derivatives". supporting information. p. 4671 - 4675. Retrieved 2019/06/17.
• 2、 Lv, Xirui,Xiang, Qinjie,Zeng, Qingle. "Potassium hydroxide-promoted selective N -monoalkylation of chiral t -butane- and p -toluenesulfinamides". . p. 164 - 175. Retrieved 2014/04/17.