t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate

Base Information

• Chemical Name: t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate
• CAS No.: 1616409-88-1
• Molecular Formula: C₃₃H₃₇F₄N₃O₇
• Molecular Weight: 663.666
• Mol file: 1616409-88-1.mol

Synonyms:

Chemical Property of t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate

There total 25 articles about t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate 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:

tert-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate + (R)-methoxytrifluoromethylphenylacetyl chloride (20445-33-4,39637-99-5) → t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate (1616409-88-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ml500069w

Reference yield:

1-vinyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid (340023-04-3) → t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate (1616409-88-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine; diphenylphosphoranyl azide / toluene / 2 h / 20 °C / Molecular sieve

1.2: 20 °C

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 5 h / 20 °C

3.1: sodium periodate / tetrahydrofuran / 0.5 h / 20 °C

4.1: lithium diisopropyl amide / tetrahydrofuran / 0.83 h / -78 °C

4.2: 1.5 h / -78 °C

4.3: CHIRALPAK IA

5.1: triethylamine; dmap / dichloromethane / 1 h / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; diphenylphosphoranyl azide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/ml500069w

Reference yield:

diethyl {[(6-methoxypyridin-3-yl)amino]methylidene}propanedioate (53241-90-0) → t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate (1616409-88-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: diphenylether / 0.08 h / 260 °C

2.1: phosphorus tribromide / N,N-dimethyl-formamide / 2.5 h / 20 °C / Cooling

3.1: sodium hydroxide / tetrahydrofuran / 3 h / 20 °C

4.1: triethylamine; diphenylphosphoranyl azide / N,N-dimethyl-formamide; tert-butyl alcohol / 1 h / 100 °C

5.1: trifluoroacetic acid / dichloromethane / 20 °C

6.1: nitrosyl tetrafluoroborate / tetrahydrofuran / 1.5 h / -10 °C

7.1: nitrosyl tetrafluoroborate / tetrahydrofuran / 1.5 h / -10 °C

7.2: 1 h / 100 °C

8.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 100 h / 100 °C

9.1: lithium diisopropyl amide / tetrahydrofuran / 0.83 h / -78 °C

9.2: 1.5 h / -78 °C

9.3: CHIRALPAK IA

10.1: triethylamine; dmap / dichloromethane / 1 h / 20 °C

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diphenylether; nitrosyl tetrafluoroborate; diphenylphosphoranyl azide; phosphorus tribromide; potassium carbonate; triethylamine; trifluoroacetic acid; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: |Curtius Rearrangement;

DOI:10.1021/ml500069w

upstream raw materials:

(1-vinyl-2-oxabicyclo[2.2.2]octan-4-yl)methanol

1-vinyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid

tert-butyl (1-ethenyl-2-oxabicyclo[2.2.2]oct-4-yl)carbamate

tert-butyl N-(4-formyl-3-oxabicyclo[2.2.2]octan-1-yl)carbamate