(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane

Base Information

Chemical Name:(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane
CAS No.:288102-63-6
Molecular Formula:C₂₆H₃₅NOSi
Molecular Weight:405.656
Hs Code.:

Synonyms:(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane

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Chemical Property of (1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane

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Technology Process of (1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane

There total 4 articles about (1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane 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%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 288102-46-5
(1S,2S,4S)-2-hydroxymethyl-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane

: 288102-63-6
(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/jo9919815

Reference yield:

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

: 288102-63-6
(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane

Guidance literature:: Multi-step reaction with 4 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

With dmap; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Acylation / 3.1: Dehydrobromination / 3.2: debenzylation / 4.1: silylation;
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

: 288102-63-6
(1S,2S,4S)-2-(tert-butyldiphenylsilyloxymethyl)-(E/Z)-5-ethylidene-1-azabicyclo[2.2.2]octane

Guidance literature:: Multi-step reaction with 3 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

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Dehydrobromination / 2.2: debenzylation / 3.1: silylation;
DOI:10.1021/jo9919815