(+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane

Base Information

Chemical Name:(+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane
CAS No.:288585-08-0
Molecular Formula:C₃₂H₅₇NO₄Si₂
Molecular Weight:575.98
Hs Code.:

Synonyms:(+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane

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Chemical Property of (+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane

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Technology Process of (+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane

There total 5 articles about (+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]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: 85.0%

: 98-88-4
benzoyl chloride

: 288585-07-9
(-)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane

: 288585-08-0
(+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/jo000348c

Reference yield:

: 532-24-1
tropinone

: 288585-08-0
(+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 4 steps

1.1: (S,S)-bis(1-phenylethyl)amine hydrochloride; n-BuLi / ethanol; hexane / 3 h / -78 °C

1.2: 72 percent / tetrahydrofuran / 3.5 h / -78 °C

2.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 7 h / 20 °C

3.1: 97 percent / Li / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C

4.1: 85 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

With 2,6-dimethylpyridine; dmap; n-butyllithium; lithium; hydrochloride salt of (1S,1'S)-bis(1-phenylethyl)amine; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; ammonia; 1.1: deprotonation / 1.2: Condensation / 2.1: silylation / 3.1: Reduction / 4.1: Acylation;
DOI:10.1021/jo000348c

Reference yield:

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 288585-08-0
(+)-(1S,2R,3R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 4 steps

1.1: (S,S)-bis(1-phenylethyl)amine hydrochloride; n-BuLi / ethanol; hexane / 3 h / -78 °C

1.2: 72 percent / tetrahydrofuran / 3.5 h / -78 °C

2.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 7 h / 20 °C

3.1: 97 percent / Li / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C

4.1: 85 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

With 2,6-dimethylpyridine; dmap; n-butyllithium; lithium; hydrochloride salt of (1S,1'S)-bis(1-phenylethyl)amine; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; ammonia; 1.1: deprotonation / 1.2: Condensation / 2.1: silylation / 3.1: Reduction / 4.1: Acylation;
DOI:10.1021/jo000348c