tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-carboxylate

Base Information

Chemical Name:tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-carboxylate
CAS No.:1354577-70-0
Molecular Formula:C₃₄H₃₅NO₃
Molecular Weight:505.657
Hs Code.:

Synonyms:tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-carboxylate

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Chemical Property of tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-carboxylate

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Technology Process of tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-carboxylate

There total 4 articles about tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-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: 78.0%

: 1354577-57-3
N⁽¹⁾-diphenylmethyl-2-piperidone-3-carboxylic acid tert-butyl ester

: 939-26-4
2-bromomethylnaphthyl bromide

: 1354577-70-0
tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-carboxylate

Guidance literature:: With (S,S)-3,3',5,5'-tetrahydro-2,6-bis(3,4,5-trifluorophenyl)-4,4'-spirobi[4H-dinaphth[2,1-c:1',2'-e]azepinium]bromide; potassium hydroxide; In toluene; at -40 ℃; for 24h; optical yield given as %ee; enantioselective reaction;
DOI:10.1002/adsc.201100542

Reference yield:

: 675-20-7
piperidin-2-one

: 1354577-70-0
tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutylammomium bromide; potassium hydroxide / toluene / 24 h / 20 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

2.2: 4 h / -78 °C

3.1: (S,S)-3,3',5,5'-tetrahydro-2,6-bis(3,4,5-trifluorophenyl)-4,4'-spirobi[4H-dinaphth[2,1-c:1',2'-e]azepinium]bromide; potassium hydroxide / toluene / 24 h / -40 °C

With (S,S)-3,3',5,5'-tetrahydro-2,6-bis(3,4,5-trifluorophenyl)-4,4'-spirobi[4H-dinaphth[2,1-c:1',2'-e]azepinium]bromide; tetrabutylammomium bromide; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1002/adsc.201100542

Reference yield:

: 776-74-9
Bromodiphenylmethane

: 1354577-70-0
tert-butyl (S)-1-benzhydryl-3-(naphthalen-2-ylmethyl)-2-oxopiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutylammomium bromide; potassium hydroxide / toluene / 24 h / 20 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

2.2: 4 h / -78 °C

3.1: (S,S)-3,3',5,5'-tetrahydro-2,6-bis(3,4,5-trifluorophenyl)-4,4'-spirobi[4H-dinaphth[2,1-c:1',2'-e]azepinium]bromide; potassium hydroxide / toluene / 24 h / -40 °C

With (S,S)-3,3',5,5'-tetrahydro-2,6-bis(3,4,5-trifluorophenyl)-4,4'-spirobi[4H-dinaphth[2,1-c:1',2'-e]azepinium]bromide; tetrabutylammomium bromide; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1002/adsc.201100542