(3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine

Base Information

Chemical Name:(3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine
CAS No.:600143-45-1
Molecular Formula:C₃₆H₅₁NOSi
Molecular Weight:541.893
Hs Code.:

Synonyms:(3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine

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Chemical Property of (3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine

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Technology Process of (3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine

There total 7 articles about (3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine 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: 84.0%

: C₁₀H₁₅BrMg

: 600143-41-7
(4R,6S,7R,10R)-7-tert-butyldimethylsilyloxy-6-methyl-octahydroquinolizidine-4-carbonitrile

: 600143-45-1
(3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine

Guidance literature:: In tetrahydrofuran; at 20 ℃;
DOI:10.1002/ejoc.200300057

Reference yield:

: 600143-37-1
(3R,5R,8R,9RS)-5-(benzyloxypropyl)-8-tert-butyldimethylsilyloxy-3-phenyloxazolo[3,2-a]piperidine

: 600143-45-1
(3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / diethyl ether; tetrahydrofuran / 48 h / 20 °C

2: 100 percent / H₂ / Pd(OH)2/C / ethanol / 96 h

3: 93 percent / potassium carbonate / acetonitrile / 12 h / Heating

4: thionyl chloride / CH₂Cl₂ / 1.5 h / Heating

5: 216 mg / LiHMDS / tetrahydrofuran / -78 °C

6: 84 percent / tetrahydrofuran / 20 °C

With thionyl chloride; hydrogen; potassium carbonate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1002/ejoc.200300057

Reference yield:

: 600143-36-0
(3R,8R,9RS)-5-(benzyloxypropyl)-8-tert-butyldimethylsilyloxy-3-phenyloxazolo[3,2-a]piperidine-5-carbonitrile

: 600143-45-1
(3E,3R,4S,6R,10R)-3-tert-butyldimethylsilyloxy-6-(dec-3-en-1-ynyl)-4-methyloctahydroquinolizidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: silver tetrafluoroborate / tetrahydrofuran / 0.25 h / 20 °C

1.2: 85 percent / zinc borohydride / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

2.1: 89 percent / diethyl ether; tetrahydrofuran / 48 h / 20 °C

3.1: 100 percent / H₂ / Pd(OH)2/C / ethanol / 96 h

4.1: 93 percent / potassium carbonate / acetonitrile / 12 h / Heating

5.1: thionyl chloride / CH₂Cl₂ / 1.5 h / Heating

6.1: 216 mg / LiHMDS / tetrahydrofuran / -78 °C

7.1: 84 percent / tetrahydrofuran / 20 °C

With silver tetrafluoroborate; thionyl chloride; hydrogen; potassium carbonate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1002/ejoc.200300057