(5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine

Base Information

Chemical Name:(5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine
CAS No.:875587-45-4
Molecular Formula:C₃₀H₄₃NOSi
Molecular Weight:461.763
Hs Code.:

Synonyms:(5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine

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Chemical Property of (5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine

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Technology Process of (5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine

There total 10 articles about (5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine 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:

: 875584-45-5
1-phenylmethyl 2-methyl 6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

: 875587-45-4
(5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / diethyl ether / -78 - -10 °C

2: 92 percent / lithium triethylborohydride / tetrahydrofuran / 0 °C

3: NaH / tetrahydrofuran / 0 - 20 °C

4: H₂ / Pd(OH)2/C / methanol / 3040 Torr

5: Me₃Al / CH₂Cl₂ / Heating

6: 91 percent / TBAF / tetrahydrofuran / 20 °C

7: LiAlH₄ / tetrahydrofuran / Heating

8: BuLi / tetrahydrofuran / 0 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; lithium triethylborohydride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3: Swern oxidation / 4: Horner-Emmons reaction / 9: Swern oxidation / 10: Wittig reaction;
DOI:10.1016/j.tetlet.2005.11.046

Reference yield:

: (2R,3S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-3-vinyl-piperidine-1-carboxylic acid benzyl ester

: 875587-45-4
(5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine

Guidance literature:: Multi-step reaction with 7 steps

1: NaH / tetrahydrofuran / 0 - 20 °C

2: H₂ / Pd(OH)2/C / methanol / 3040 Torr

3: Me₃Al / CH₂Cl₂ / Heating

4: 91 percent / TBAF / tetrahydrofuran / 20 °C

5: LiAlH₄ / tetrahydrofuran / Heating

6: BuLi / tetrahydrofuran / 0 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; 1: Horner-Emmons reaction / 6: Swern oxidation / 7: Wittig reaction;
DOI:10.1016/j.tetlet.2005.11.046

Reference yield:

: 875587-39-6
phenylmethyl 6-(tert-butyldiphenylsilyloxymethyl)-2-hydroxymethyl-3-vinylpiperidine-1-carboxylate

: 875587-45-4
(5S,8R,8aS)-5-[(Z)-4-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-8-ethyl-octahydro-indolizine

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / tetrahydrofuran / 0 - 20 °C

2: H₂ / Pd(OH)2/C / methanol / 3040 Torr

3: Me₃Al / CH₂Cl₂ / Heating

4: 91 percent / TBAF / tetrahydrofuran / 20 °C

5: LiAlH₄ / tetrahydrofuran / Heating

6: BuLi / tetrahydrofuran / 0 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; 1: Swern oxidation / 2: Horner-Emmons reaction / 7: Swern oxidation / 8: Wittig reaction;
DOI:10.1016/j.tetlet.2005.11.046