(3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine

Base Information

Chemical Name:(3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine
CAS No.:600143-44-0
Molecular Formula:C₃₄H₄₁NOSi
Molecular Weight:507.791
Hs Code.:

Synonyms:(3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine

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Technology Process of (3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine

There total 7 articles about (3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine 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: 89.0%

: 6738-06-3
phenylethynylmagnesium bromide

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

: 600143-44-0
(3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine

Guidance literature:: In tetrahydrofuran; at 20 ℃;
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

: 600143-44-0
(3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine

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: 89 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

Reference yield:

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

: 600143-44-0
(3R,4S,6R,10R)-6-ethynyl-3-tert-butyldimethylsilyloxy-4-methyl-6-(phenylethynyl)octahydroquinolizidine

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: 89 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