tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate
CAS No.:1312350-26-7
Molecular Formula:C₃₂H₄₄BrN₃O₅
Molecular Weight:630.622
Hs Code.:

tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

Synonyms:tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

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Chemical Property of tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

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Technology Process of tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

There total 31 articles about tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate 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:

: 1312350-23-4
(3R,4S)-1-(tert-butoxycarbonyl)-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-3-carboxylic acid

: 1194491-85-4
N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine mesylate

: 1312350-26-7
tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

Guidance literature:: (3R,4S)-1-(tert-butoxycarbonyl)-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-3-carboxylic acid; With 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; In 2-methyltetrahydrofuran; acetonitrile; at -19.9 - -2.9 ℃; for 1.33333h; Inert atmosphere; Large scale reaction;

N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine mesylate; In 2-methyltetrahydrofuran; dichloromethane; acetonitrile; at 3 - 20 ℃; Inert atmosphere; Large scale reaction;
DOI:10.1021/op2001063

Reference yield:

: 1194488-90-8
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

: 1312350-26-7
tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / propan-1-ol; water / 14 h / 8 °C

2: methanol; magnesium / 2 h / Sonication

3: sodium ethanolate / ethanol / 16 h / 80 °C

4: sodium iodide / acetonitrile / 72 h / 45 °C

5: chiral AD column / ethanol; hexane; isopropyl alcohol / Resolution of racemate

6: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h

7: HATU / N,N-dimethyl-formamide

With methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium ethanolate; sodium carbonate; magnesium; HATU; sodium iodide; lithium hydroxide; In tetrahydrofuran; methanol; propan-1-ol; ethanol; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 1: Suzuki coupling;
DOI:10.1016/j.bmcl.2011.05.013

Reference yield:

: 1229244-21-6
1-tert-butyl 3-ethyl 2'-methoxy-5,6-dihydro-4,4'-bipyridine-1,3(2H)-dicarboxylate

: 1312350-26-7
tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: methanol; magnesium / 2 h / Sonication

2: sodium ethanolate / ethanol / 16 h / 80 °C

3: sodium iodide / acetonitrile / 72 h / 45 °C

4: chiral AD column / ethanol; hexane; isopropyl alcohol / Resolution of racemate

5: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h

6: HATU / N,N-dimethyl-formamide

With methanol; water; sodium ethanolate; magnesium; HATU; sodium iodide; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;
DOI:10.1016/j.bmcl.2011.05.013