(-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one

Base Information

Chemical Name:(-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one
CAS No.:646996-58-9
Molecular Formula:C₂₂H₃₄BrNO₄SSi
Molecular Weight:516.572
Hs Code.:

Synonyms:(-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one

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Chemical Property of (-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one

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Technology Process of (-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one

There total 6 articles about (-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one 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: 74.0%

: 353248-31-4
(+)-(5S)-1-[5-(tert-butyldimethylsilyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]-cyclobutanol

: (-)-(5S,8S,10R)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one

: 646996-58-9
(-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one

Guidance literature:: With N-Bromosuccinimide; methyloxirane; In isopropyl alcohol; at -78 - 20 ℃; for 3h;
DOI:10.1021/jo0493572

Reference yield:

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

: 646996-58-9
(-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / imidazole / dimethylformamide / 13 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 75 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

3.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / -78 °C

3.2: 76 percent / tetrahydrofuran; toluene / -78 - 20 °C

4.1: 74 percent / propylene oxide; N-bromosuccinimide / propan-2-ol / 3 h / -78 - 20 °C

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; potassium hexamethylsilazane; methyloxirane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1021/jo0493572

Reference yield:

: 87179-81-5
(-)-(5S)-5-(tert-butyldimethylsilanyloxy)piperidin-2-one

: 646996-58-9
(-)-(5R,8S,10S)-10-bromo-8-[tert-butyldimethylsilyloxy]-6-[toluene-4-sulfonyl]-6-azaspiro[4.5]decan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 75 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / -78 °C

2.2: 76 percent / tetrahydrofuran; toluene / -78 - 20 °C

3.1: 74 percent / propylene oxide; N-bromosuccinimide / propan-2-ol / 3 h / -78 - 20 °C

With N-Bromosuccinimide; n-butyllithium; potassium hexamethylsilazane; methyloxirane; In tetrahydrofuran; hexane; isopropyl alcohol; toluene;
DOI:10.1021/jo0493572