(1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene

Base Information

Chemical Name:(1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene
CAS No.:1146974-31-3
Molecular Formula:C₁₈H₂₂O₂
Molecular Weight:270.371
Hs Code.:

Synonyms:(1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene

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Chemical Property of (1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene

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Technology Process of (1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene

There total 11 articles about (1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene 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: 74.0%

: 1146974-30-2
(1R,5R,6S)-6-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-7-one

: 1146974-31-3
(1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene

Guidance literature:: (1R,5R,6S)-6-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-7-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -40 ℃; Inert atmosphere;

With N,N-phenylbistrifluoromethane-sulfonimide; In tetrahydrofuran; at -40 ℃; for 0.5h; Further stages; Inert atmosphere;
DOI:10.1021/ol900441f

Reference yield:

: C₁₉H₂₁F₃O₅S

: 1146974-31-3
(1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene

Guidance literature:: C₁₉H₂₁F₃O₅S; With tributyl-amine; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

With formic acid; In N,N-dimethyl-formamide; at 60 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol502543r

Reference yield:

: (1R,2'S,5S)-spiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-7-one

: 1146974-31-3
(1R,5S,8S)-8-benzylspiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-6-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: (R,R)-N,N-bis-(1-phenylethyl)amine; n-butyllithium; lithium chloride / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 3 h / 50 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / ethanol / 2.5 h / 20 °C

5.1: lithium hexamethyldisilazane; N,N-phenylbistrifluoromethane-sulfonimide / tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere

5.2: 0.5 h / 20 °C / Inert atmosphere

5.3: 1 h / 60 °C / Inert atmosphere

With n-butyllithium; N,N-phenylbistrifluoromethane-sulfonimide; palladium 10% on activated carbon; hydrogen; (R,R)-N,N-bis-(1-phenylethyl)amine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/ja509766f