(S,R_S)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide

Base Information

• Chemical Name: (S,R_S)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide
• CAS No.: 1609692-17-2
• Molecular Formula: C₂₄H₃₆BrNO₂SSi
• Molecular Weight: 510.611

Synonyms:(S,R_S)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide

Chemical Property of (S,R_S)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide

Chemical Property:

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Technology Process of (S,R_S)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide

There total 1 articles about (S,R_S)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-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: 93.0%

(R)-N-(2-bromobenzyliden)-N-(tert-butanesulfinyl)amine (1015198-51-2) + (3-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)magnesium bromide (118892-45-8) → (S,RS)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide (1609692-17-2)

Guidance literature:

In tetrahydrofuran; at -48 ℃; for 3h; stereoselective reaction;

DOI:10.1039/c4cc01831a

Reference yield: 86.0%

(S,RS)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide (1609692-17-2) → (S,SS)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide (1609692-27-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 6h;

DOI:10.1039/c4cc01831a

Reference yield:

(S,RS)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide (1609692-17-2) → (S)-3-(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)-2,3-dihydrobenzo[d]isothiazole-1,1-dioxide (1166859-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 6 h / 110 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;

DOI:10.1039/c4cc01831a

upstream raw materials:

(R)-N-(2-bromobenzyliden)-N-(tert-butanesulfinyl)amine

(3-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)magnesium bromide

Downstream raw materials:

(S,S_S)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide

(S)-3-(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)-2,3-dihydrobenzo[d]isothiazole-1,1-dioxide

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