3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester
CAS No.:744216-09-9
Molecular Formula:C₂₃H₂₈N₄O₃
Molecular Weight:408.5
Hs Code.:

3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2<i>H</i>-[3,4']bipyridinyl-1-carboxylic acid <i>tert</i>-butyl ester

Synonyms:3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

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Chemical Property of 3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

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Technology Process of 3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

There total 8 articles about 3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester 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: 82.0%

: 744216-07-7
6'-(2-benzyloxy-phenyl)-3'-cyano-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

: 744216-09-9
3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; at 20 ℃; for 24h; under 2280 Torr;
DOI:10.1016/j.bmcl.2004.05.040

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 744216-09-9
3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / aq. NaOH / dioxane / 12 h / 20 °C

2: 100 percent / PyBOP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

3: LiAlH₄ / tetrahydrofuran / 0.5 h / -15 °C

4: 34 percent / NH₄OAc / toluene / 2 h / 150 °C

5: 45 percent / CuBr₂; t-butyl nitrite / acetonitrile / 2 h / 65 °C

6: 58 percent / Et₃N / dimethylsulfoxide / 12 h / 40 °C

7: 82 percent / H₂ / Pd/C / ethyl acetate; tetrahydrofuran / 24 h / 20 °C / 2280 Torr

With sodium hydroxide; lithium aluminium tetrahydride; tert.-butylnitrite; ammonium acetate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; copper(ll) bromide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/j.bmcl.2004.05.040

Reference yield:

: 71381-75-4,88495-54-9,84358-12-3
N-(tert-butyloxycarbonyl)nipecotic acid

: 744216-09-9
3'-cyano-6'-(2-hydroxy-phenyl)-2'-methylamino-3,4,5,6-tetrahydro-2H-[3,4']bipyridinyl-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / PyBOP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

2: LiAlH₄ / tetrahydrofuran / 0.5 h / -15 °C

3: 34 percent / NH₄OAc / toluene / 2 h / 150 °C

4: 45 percent / CuBr₂; t-butyl nitrite / acetonitrile / 2 h / 65 °C

5: 58 percent / Et₃N / dimethylsulfoxide / 12 h / 40 °C

6: 82 percent / H₂ / Pd/C / ethyl acetate; tetrahydrofuran / 24 h / 20 °C / 2280 Torr

With lithium aluminium tetrahydride; tert.-butylnitrite; ammonium acetate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; copper(ll) bromide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/j.bmcl.2004.05.040