(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-one

Base Information

Chemical Name:(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-one
CAS No.:288102-68-1
Molecular Formula:C₂₄H₃₁NO₂Si
Molecular Weight:393.601
Hs Code.:

Synonyms:(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-one

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Chemical Property of (1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-one

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Technology Process of (1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-one

There total 7 articles about (1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-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: 90.0%

: 288102-65-8
(1S,2S,4S,5R/S,10R/S)-2-(tert-butyldiphenylsilyloxymethyl)-5-(5,10-dihydroxyethyl)-1-azabicyclo[2.2.2]octane

: 288102-68-1
(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-one

Guidance literature:: With sodium periodate; In water; tert-butyl alcohol; at 20 ℃; for 2h;
DOI:10.1021/jo9919815

Reference yield:

: (2S,4S,5R)-2-hydroxymethyl-5-vinylquinuclidine

: 288102-68-1
(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / aq. HBr / 96 h / 20 °C

2.1: 88 percent / Et₃N / CH₂Cl₂ / 14 h / 20 °C

3.1: DBU / dimethylformamide / 3 h / 110 °C

3.2: 63 percent / K₂CO₃ / methanol / 0.33 h / 20 °C

4.1: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

5.1: 84 percent / OsO₄; K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

6.1: 90 percent / NaIO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; hydrogen bromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium hexacyanoferrate(III); In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Addition / 2.1: Acylation / 3.1: Dehydrobromination / 3.2: debenzylation / 4.1: silylation / 5.1: Oxidation / 6.1: Oxidation;
DOI:10.1021/jo9919815

Reference yield:

: 288102-44-3
(1S,2S,4S,5R,10R/S)-2-hydroxymethyl-5-(10-bromoethyl)-1-azabicyclo[2.2.2]octane

: 288102-68-1
(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-1-azabicyclo[2.2.2]octan-5-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / Et₃N / CH₂Cl₂ / 14 h / 20 °C

2.1: DBU / dimethylformamide / 3 h / 110 °C

2.2: 63 percent / K₂CO₃ / methanol / 0.33 h / 20 °C

3.1: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

4.1: 84 percent / OsO₄; K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

5.1: 90 percent / NaIO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium hexacyanoferrate(III); In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Acylation / 2.1: Dehydrobromination / 2.2: debenzylation / 3.1: silylation / 4.1: Oxidation / 5.1: Oxidation;
DOI:10.1021/jo9919815