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

Base Information

• Chemical Name: (2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine
• CAS No.: 757247-76-0
• Molecular Formula: C₂₅H₄₀ClN₃O₃Si
• Molecular Weight: 494.149
• Mol file: 757247-76-0.mol

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

Chemical Property of (2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine

There total 16 articles about (2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine 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: 99.0%

(2R,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-((1S)-1-aminoethyl)-pyrrolidine (757247-74-8) + 2-chloro-4-iodo-3-methylbenzonitrile (757247-75-9) → (2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine (757247-76-0)

Guidance literature:

With caesium carbonate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In dimethyl sulfoxide; toluene; at 110 ℃;

DOI:10.1016/j.bmcl.2007.06.007

Reference yield:

(2R,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-((1S)-1-aminoethyl)-pyrrolidine (757247-74-8) + 2-chloro-4-iodo-3-methylbenzonitrile (757247-75-9) + (S)-N,N-dimethyl-1-[(R)-2-(diphenyphosphino)ferrocenyl]ethylamine → (2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine (757247-76-0)

Guidance literature:

With caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In dimethyl sulfoxide; toluene; at 20 - 110 ℃; for 48.5h;

Reference yield:

(2R,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyethyl)-pyrrolidine (864271-14-7) → (2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine (757247-76-0)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; hydroxylamine hydrochloride; ammonia; hydrogen; caesium carbonate; 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

upstream raw materials:

(2R,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-((1S)-1-aminoethyl)-pyrrolidine

2-chloro-4-iodo-3-methylbenzonitrile

4-amino-2-chloro-3-methyl-benzonitrile

(2S,3S)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-pyrrolidinecarboxylic acid methyl ester

Downstream raw materials:

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

C₂₀H₃₀N₃SO₃SiCl

(2R,3S)-3-(tert-butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine, trifluoroacetic acid salt

2-chloro-4-((1S,7S,7aR)-7-hydroxy-1-methyl-3-oxo-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-3-methylbenzonitrile