4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile

Base Information

Chemical Name:4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile
CAS No.:757247-77-1
Molecular Formula:C₂₀H₃₂ClN₃OSi
Molecular Weight:394.032
Hs Code.:

Synonyms:4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile

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Chemical Property of 4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile

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Technology Process of 4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile

There total 16 articles about 4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile 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: 44.0%

: 757247-76-0
(2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine

: 757247-77-1
4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃;
DOI:10.1016/j.bmcl.2007.06.007

Reference yield:

: 757247-75-9
2-chloro-4-iodo-3-methylbenzonitrile

: 757247-77-1
4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / (S)-N,N-diMe₂-1-[(R)-2-(PPh₂)ferrocenyl]ethylamine; Cs₂CO₃ / Pd₂(dba)3 / dimethylsulfoxide; toluene / 110 °C

2: 44 percent / TFA / CH₂Cl₂ / 20 °C

With caesium carbonate; trifluoroacetic acid; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/j.bmcl.2007.06.007

Reference yield:

: 864271-14-7
(2R,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyethyl)-pyrrolidine

: 757247-77-1
4-((S)-1-((2R,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidin-2-yl)ethylamino)-2-chloro-3-methylbenzonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: NMO; TPAP / acetonitrile; CH₂Cl₂ / 20 °C

2: NH₂OH*HCl; pyridine / methanol; H₂O / 20 °C

3: 64 percent / H₂; NH₃ / Pd/C; Raney-Ni / methanol; H₂O / 20 °C / 3620.13 Torr

4: 99 percent / (S)-N,N-diMe₂-1-[(R)-2-(PPh₂)ferrocenyl]ethylamine; Cs₂CO₃ / Pd₂(dba)3 / dimethylsulfoxide; toluene / 110 °C

5: 44 percent / TFA / CH₂Cl₂ / 20 °C

With pyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; hydroxylamine hydrochloride; ammonia; hydrogen; caesium carbonate; trifluoroacetic acid; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; nickel; In methanol; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1016/j.bmcl.2007.06.007