(2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine

Base Information

Chemical Name:(2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine
CAS No.:1333213-20-9
Molecular Formula:C₂₃H₃₉NO₃Si
Molecular Weight:405.653
Hs Code.:

Synonyms:(2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine

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Chemical Property of (2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine

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Technology Process of (2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine

There total 12 articles about (2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine 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: 75.0%

: 1333213-19-6
4-((2S,4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(3,4-dimethoxyphenyl)piperidine-2-yl)butane-1-ol

: 1333213-20-9
(2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -5 - 20 ℃; for 6.08333h; Inert atmosphere;
DOI:10.1021/ol2019967

Reference yield:

: 1333213-03-8
C₁₈H₂₅NO₄

: 1333213-20-9
(2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine

Guidance literature:: Multi-step reaction with 11 steps

1.1: diethyl ether / 12.5 h / -30 °C / Inert atmosphere

2.1: sodium tungstate heptahydrate; dihydrogen peroxide / water; acetone / 12 h

3.1: toluene / 30 h / Reflux; Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; water / 3 h / 0 °C

5.1: sodium periodate / water; acetonitrile / 0.5 h / 5 - 10 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 - 0 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C

8.1: acetic acid; zinc / water / 0.17 h / 20 °C

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.67 h / 0 °C

10.1: hydrogen; palladium(II) hydroxide; trifluoroacetic acid / tetrahydrofuran; methanol / 7 h / 760.05 Torr

11.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 6.08 h / -5 - 20 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; n-butyllithium; palladium 10% on activated carbon; sodium tungstate heptahydrate; hydrogen; dihydrogen peroxide; palladium(II) hydroxide; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; acetonitrile; 6.1: Wittig reaction / 6.2: Wittig reaction / 11.1: Mitsunobu reaction;
DOI:10.1021/ol2019967

Reference yield:

: 5763-61-1
3,4-dimethoxybenzylamine

: 1333213-20-9
(2R,4S,9aS)-2-(tert-butyldimethylsilyloxy)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizine

Guidance literature:: Multi-step reaction with 12 steps

1.1: magnesium sulfate / tetrahydrofuran / 0.17 h / 5 °C / Inert atmosphere

1.2: 5 - 20 °C / Inert atmosphere

2.1: diethyl ether / 12.5 h / -30 °C / Inert atmosphere

3.1: sodium tungstate heptahydrate; dihydrogen peroxide / water; acetone / 12 h

4.1: toluene / 30 h / Reflux; Inert atmosphere

5.1: hydrogenchloride / tetrahydrofuran; water / 3 h / 0 °C

6.1: sodium periodate / water; acetonitrile / 0.5 h / 5 - 10 °C

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 - 0 °C / Inert atmosphere

7.2: -78 - 20 °C / Inert atmosphere

8.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C

9.1: acetic acid; zinc / water / 0.17 h / 20 °C

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.67 h / 0 °C

11.1: hydrogen; palladium(II) hydroxide; trifluoroacetic acid / tetrahydrofuran; methanol / 7 h / 760.05 Torr

12.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 6.08 h / -5 - 20 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; n-butyllithium; palladium 10% on activated carbon; sodium tungstate heptahydrate; hydrogen; dihydrogen peroxide; palladium(II) hydroxide; magnesium sulfate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; acetonitrile; 7.1: Wittig reaction / 7.2: Wittig reaction / 12.1: Mitsunobu reaction;
DOI:10.1021/ol2019967