(S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile

Base Information

• Chemical Name: (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile
• CAS No.: 159848-75-6
• Molecular Formula: C₁₅H₂₀N₂O₃
• Molecular Weight: 276.335
• Mol file: 159848-75-6.mol

Synonyms:(S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile

Chemical Property of (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile

There total 5 articles about (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile 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: 86.0%

2-(naphthalene-2-ylsulfonyl)acetonitrile (32083-60-6) + N-tert-butyl 4-methoxybenzylidenecarbamate (479423-40-0) → (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile (159848-75-6)

Guidance literature:

2-(naphthalene-2-ylsulfonyl)acetonitrile; N-tert-butyl 4-methoxybenzylidenecarbamate; With (9H-fluoren-9-yl)methyl ((S)-1-(3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)ureido)-2,2-dimethylpropyl)carbamate; In dichloromethane; at -40 ℃; Inert atmosphere;

With chloro-trimethyl-silane; magnesium; ethylene dibromide; In methanol; dichloromethane; at 0 - 20 ℃; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201304877

Reference yield: 83.0%

potassium cyanide (151-50-8) + (R)-2-tert-butoxycarbonylamino-1-methanesulfonyloxy-2-(4-methoxyphenyl)ethane (159990-11-1) → (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile (159848-75-6)

Guidance literature:

With 18-crown-6 ether; In dimethyl sulfoxide; at 50 ℃; for 3h;

DOI:10.1016/S0040-4020(01)85520-4

Reference yield:

2-(phenylsulfonyl)acetonitrile (7605-28-9) + N-tert-butyl 4-methoxybenzylidenecarbamate (479423-40-0) → (R)-3-(N-tert-butoxycarbonylamino)-3-(4'-methoxyphenyl)propanitrile (1227402-93-8) + (S)-3-(N-terc-butoxycarbonylamine)-3-(4-methoxyphenyl)propanenitrile (159848-75-6)

Guidance literature:

2-(phenylsulfonyl)acetonitrile; N-tert-butyl 4-methoxybenzylidenecarbamate; With (DHQ)2PYR; In dichloromethane; at -50 ℃; for 18h; Inert atmosphere;

With chloro-trimethyl-silane; magnesium; In methanol; ethylene dibromide; at 0 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo1005872

upstream raw materials:

potassium cyanide

(R)-2-tert-butoxycarbonylamino-1-methanesulfonyloxy-2-(4-methoxyphenyl)ethane

1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate

methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)acetate

Downstream raw materials:

(S)-β-amino-β-(4-methoxyphenyl)propionic acid

C₁₅H₂₄N₂O₃

(3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

(3S,3S')-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane