(2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide

Base Information

Chemical Name:(2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide
CAS No.:249259-94-7
Molecular Formula:C₁₂H₂₀N₂O₂
Molecular Weight:224.303
Hs Code.:

Synonyms:(2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide

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Chemical Property of (2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide

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Technology Process of (2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide

There total 1 articles about (2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide 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:

: 207129-35-9
[(2R,4S,5R)-2-hydroxymethyl-5-vinyl-2-quinuclidine]

: 249259-94-7
(2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide

Guidance literature:: Multi-step reaction with 3 steps

1: Jones reagent / acetone / 72 h / Heating

2: 61 mg / hydrochloric acid / 72 h / Heating

3: 59 percent / Me₂AlCl / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; jones reagent; dimethylaluminum chloride; In dichloromethane; acetone;
DOI:10.1021/ol990981o

Reference yield:

: 249259-94-7
(2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide

: (aS,2R,4S,5R)-1-[4-(trifluoromethyl)benzyl]-2-[(R)-(2,2'-dimethoxy-3'-(methoxymethyl)-1,1'-binaphthalen-7-yl)hydroxymethyl]-5-ethylazoniabicyclo[2.2.2]octane bromide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 99 percent / H₂ / 10 percent Pd/C / ethanol / 3 h / 1500.12 Torr

2.1: BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 10 percent / DIBAL-H / benzene; hexane / 4 h / 20 °C

3.1: 12 percent / tetrahydrofuran / 72 h / Heating

With n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; 1.1: Reduction / 2.1: Acylation / 2.2: Reduction / 3.1: Alkylation;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<981::AID-HLCA981>3.0.CO;2-V

Reference yield:

: 249259-94-7
(2R,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]octane-2-carboxylic acid N-methoxy-N-methylamide

: (aS,2R,4S,5R)-1-[4-(trifluoromethyl)benzyl]-2-[(S)-(2,2'-dimethoxy-3'-(methoxymethyl)-1,1'-binaphthalen-7-yl)hydroxymethyl]-5-ethylazoniabicyclo[2.2.2]octane bromide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 99 percent / H₂ / 10 percent Pd/C / ethanol / 3 h / 1500.12 Torr

2.1: BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 12 percent / DIBAL-H / benzene; hexane / 4 h / 20 °C

3.1: 50 percent / tetrahydrofuran / 72 h / Heating

With n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; 1.1: Reduction / 2.1: Acylation / 2.2: Reduction / 3.1: Alkylation;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<981::AID-HLCA981>3.0.CO;2-V