tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate

Base Information

Chemical Name:tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate
CAS No.:176966-78-2
Molecular Formula:C₂₆H₃₃NO₄Si
Molecular Weight:451.638
Hs Code.:

Synonyms:tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate

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Chemical Property of tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate

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Technology Process of tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate

There total 6 articles about tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-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: 60.0%

: 176966-77-1
tert-butyl (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one-1-carboxylate

: 176966-78-2
tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate

Guidance literature:: tert-butyl (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one-1-carboxylate; With n-butyllithium; hexamethyldisilazan; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With Phenylselenyl chloride; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1016/j.tetlet.2013.07.042

Reference yield:

: 24211-54-9
(S)-5-hydroxypiperidin-2-one

: 176966-78-2
tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

2: 1.) 1,4-diazabicyclo<2.2.2>octane, n-butyl lithium / 1.) THF, hexane, -78 deg C, 45 min, 2.) THF, hexane, -78 deg C, 2 h

3: 1.) LiHMDS / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 2h

4: 30percent hydrogen peroxide / ethyl acetate / 0.75 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; n-butyllithium; dihydrogen peroxide; lithium hexamethyldisilazane; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/0957-4166(96)00085-7

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 176966-78-2
tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

2: 1.) 1,4-diazabicyclo<2.2.2>octane, n-butyl lithium / 1.) THF, hexane, -78 deg C, 45 min, 2.) THF, hexane, -78 deg C, 2 h

3: 1.) LiHMDS / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 2h

4: 30percent hydrogen peroxide / ethyl acetate / 0.75 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; n-butyllithium; dihydrogen peroxide; lithium hexamethyldisilazane; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/0957-4166(96)00085-7