(R_S,R)-N-(2-methyl-1-phenylpropyl)-2-methylpropane-2-sulfinamide

Base Information

• Chemical Name: (R_S,R)-N-(2-methyl-1-phenylpropyl)-2-methylpropane-2-sulfinamide
• CAS No.: 196929-93-8
• Molecular Formula: C₁₄H₂₃NOS
• Molecular Weight: 253.409
• Mol file: 196929-93-8.mol

Synonyms:(R_S,R)-N-(2-methyl-1-phenylpropyl)-2-methylpropane-2-sulfinamide

Chemical Property of (R_S,R)-N-(2-methyl-1-phenylpropyl)-2-methylpropane-2-sulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R_S,R)-N-(2-methyl-1-phenylpropyl)-2-methylpropane-2-sulfinamide

There total 12 articles about (R_S,R)-N-(2-methyl-1-phenylpropyl)-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: 91.0%

(R)-N-benzylidene-2-methylpropane-2-sulfinamide (196929-85-8) + 2-iodo-propane (75-30-9) → (RS,R)-N-(2-methyl-1-phenylpropyl)-2-methylpropane-2-sulfinamide (196929-93-8)

Guidance literature:

(R)-N-benzylidene-2-methylpropane-2-sulfinamide; With boron trifluoride diethyl etherate; In dichloromethane; for 0.0833333h; Inert atmosphere;

2-iodo-propane; With triethyl borane; oxygen; tri-n-butyl-tin hydride; In hexane; dichloromethane; at -78 ℃; for 1.1h; Inert atmosphere;

DOI:10.1021/ol400439g

Reference yield: 91.0%

2-iodo-propane (75-30-9) + (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide (186249-76-3) → (RS,R)-N-(2-methyl-1-phenylpropyl)-2-methylpropane-2-sulfinamide (196929-93-8)

Guidance literature:

With triethyl borane; boron trifluoride diethyl etherate; oxygen; tri-n-butyl-tin hydride; In hexane; dichloromethane; at -78 ℃; for 1.1h; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201402355

Reference yield:

benzaldehyde (100-52-7) → (RS,R)-N-(2-methyl-1-phenylpropyl)-2-methylpropane-2-sulfinamide (196929-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / MgSO₄ / CH₂Cl₂

2: CH₂Cl₂; diethyl ether

With magnesium sulfate; In diethyl ether; dichloromethane;

DOI:10.1021/ja972012z

upstream raw materials:

isopropylmagnesium bromide

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

phenylmagnesium bromide

(R,E)-2-methyl-N-(2-methylpropylidene)propane-2-sulfinamide

Downstream raw materials:

C₁₇H₁₉NO

(R)-2-methyl-1-phenylpropylamine

(R)-2-methyl-1-phenylpropylamine hydrochloride

Refernces

• 1、 Guijarro, David,Pablo, óscar,Yus, Miguel. "Synthesis of highly enantiomerically enriched amines by asymmetric transfer hydrogenation of N-(tert-Butylsulfinyl)imines". . p. 338 - 349. Retrieved 2014/04/03.
• 2、 Pablo, Oscar,Guijarro, David,Kovacs, Gabor,Lledos, Agusti,Ujaque, Gregori,Yus, Miguel. "A versatile Ru catalyst for the asymmetric transfer hydrogenation of both aromatic and aliphatic sulfinylimines". supporting information; experimental part. p. 1969 - 1983. Retrieved 2012/03/26.