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

Base Information

Chemical Name:(+)-(1S,2R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-one
CAS No.:288585-06-8
Molecular Formula:C₂₅H₅₁NO₃Si₂
Molecular Weight:469.856
Hs Code.:

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

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

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

There total 1 articles about (+)-(1S,2R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-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: 96.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 288585-05-7
(+)-(1S,2R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-hydroxy)ethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-one

: 288585-06-8
(+)-(1S,2R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 7h;
DOI:10.1021/jo000348c

Reference yield:

: 288585-06-8
(+)-(1S,2R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-one

: 47195-07-3
(+)-cocaine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / Li / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C

2.1: 85 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

3.1: 50percent HF / acetonitrile; H₂O / 1 h / 20 °C

4.1: NaIO₄ / RuCl₃*3H₂O / CCl₄; acetonitrile; H₂O / 3 h / 20 °C

4.2: benzene; methanol; hexane / 3 h / 20 °C

With dmap; sodium periodate; lithium; triethylamine; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; ammonia; water; acetonitrile; 1.1: Reduction / 2.1: Acylation / 3.1: desilylation / 4.1: Oxidation / 4.2: Methylation;
DOI:10.1021/jo000348c

Reference yield:

: 288585-06-8
(+)-(1S,2R,5R,1'S)-2-[(2'-tert-butyldimethylsiloxy-1'-triisopropylsiloxy)ethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-one

: Benzoic acid (1S,2S,3S,6R,8R)-11-methyl-5-oxa-11-aza-tricyclo[6.2.1.0^2,6]undec-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / Li / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C

2.1: 85 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

3.1: 50percent HF / acetonitrile; H₂O / 1 h / 20 °C

4.1: NaIO₄ / RuCl₃*3H₂O / CCl₄; acetonitrile; H₂O / 3 h / 20 °C

4.2: benzene; methanol; hexane / 3 h / 20 °C

With dmap; sodium periodate; lithium; triethylamine; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; ammonia; water; acetonitrile; 1.1: Reduction / 2.1: Acylation / 3.1: desilylation / 4.1: Oxidation / 4.2: Methylation;
DOI:10.1021/jo000348c