N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide

Base Information

Chemical Name:N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide
CAS No.:372965-96-3
Molecular Formula:C₃₉H₃₉N₃O₂
Molecular Weight:581.758
Hs Code.:

Synonyms:N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide

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Chemical Property of N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide

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Technology Process of N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide

There total 7 articles about N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide 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:

: N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-triisopropylsilanyloxy-methyl]-quinolin-6-yl}-benzamide

: 372965-96-3
N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 1h;
DOI:10.1021/ol016577i

Reference yield:

: 1013-88-3
Benzophenone imine

: 372965-96-3
N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / BINAP; Cs₂CO₃ / Pd(OAc)2 / tetrahydrofuran / 23 h / 70 °C

2: NaCNBH₃ / acetic acid / 5.5 h / 23 °C

3: pyridine / 2 h / 23 °C

4: 1.26 g / TBAF / tetrahydrofuran / 1 h / 23 °C

With pyridine; tetrabutyl ammonium fluoride; sodium cyanoborohydride; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; In tetrahydrofuran; acetic acid;
DOI:10.1021/ol016577i

Reference yield:

: dihydrocupreidine

: 372965-96-3
N-Benzhydryl-N-{4-[(S)-((2R,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-hydroxy-methyl]-quinolin-6-yl}-benzamide

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / DMAP; 2,4,6-collidine / CH₂Cl₂ / 24 h / Heating

2: 90 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / 23 °C

3: 91 percent / BINAP; Cs₂CO₃ / Pd(OAc)2 / tetrahydrofuran / 23 h / 70 °C

4: NaCNBH₃ / acetic acid / 5.5 h / 23 °C

5: pyridine / 2 h / 23 °C

6: 1.26 g / TBAF / tetrahydrofuran / 1 h / 23 °C

With pyridine; 2,4,6-trimethyl-pyridine; dmap; tetrabutyl ammonium fluoride; sodium cyanoborohydride; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; acetic acid;
DOI:10.1021/ol016577i