[trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester
• CAS No.: 1416224-51-5
• Molecular Formula: C₂₃H₃₁N₃O₄
• Molecular Weight: 413.517
• Mol file: 1416224-51-5.mol

Synonyms:[trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester

Chemical Property of [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester

There total 12 articles about [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester 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: 49.0%

{trans-4-[2-hydroxy-3-(3-hydroxy-6-methoxy-[1,5]naphthyridin-4-yl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester (1416224-49-1) → [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester (1416224-51-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 25 ℃; for 1h;

Reference yield:

8-bromo-7-chloro-2-methoxy-1,5-naphthyridine (915976-85-1) → [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester (1416224-51-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: N,N-dimethyl-formamide / 8 h / 130 °C

2.1: sodium hydride / tetrahydrofuran / 2 h / -30 °C

3.1: sodium hydroxide; dihydrogen peroxide / manganese(IV) oxide / water; methanol / 1 h / 70 °C

4.1: Schwartz's reagent / tetrahydrofuran / 0.17 h / 18 - 25 °C

5.1: phosphorus tribromide / dichloromethane / 1 h / 18 - 25 °C

5.2: pH 7

6.1: toluene / 6 h / Reflux

7.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C

7.2: 15 h / 18 - 25 °C

8.1: 4-methylmorpholine N-oxide / potassium osmate(VI) dihydrate / water; acetone / 15 h / 18 - 25 °C

9.1: toluene / 2 h / 70 °C

10.1: triethylamine; hydrogen / palladium-on-charcoal / methanol / 1 h / 18 - 25 °C / 750.08 Torr

11.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 25 °C

With Schwartz's reagent; hydrogen; dihydrogen peroxide; phosphorus tribromide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; manganese(IV) oxide; potassium osmate(VI) dihydrate; palladium-on-charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 11.1: Mitsunobu reaction;

Reference yield:

3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-carbonitrile (1312577-92-6) → [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester (1416224-51-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydroxide; dihydrogen peroxide / manganese(IV) oxide / water; methanol / 1 h / 70 °C

2.1: Schwartz's reagent / tetrahydrofuran / 0.17 h / 18 - 25 °C

3.1: sodium tetrahydroborate / methanol / 0.08 h / 18 - 25 °C

4.1: phosphorus tribromide / dichloromethane / 1 h / 18 - 25 °C

4.2: pH 7

5.1: toluene / 6 h / Reflux

6.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C

6.2: 15 h / 18 - 25 °C

7.1: 4-methylmorpholine N-oxide / potassium osmate(VI) dihydrate / water; acetone / 15 h / 18 - 25 °C

8.1: toluene / 2 h / 70 °C

9.1: triethylamine; hydrogen / palladium-on-charcoal / methanol / 1 h / 18 - 25 °C / 750.08 Torr

10.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 25 °C

With sodium tetrahydroborate; Schwartz's reagent; hydrogen; dihydrogen peroxide; phosphorus tribromide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; manganese(IV) oxide; potassium osmate(VI) dihydrate; palladium-on-charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 10.1: Mitsunobu reaction;

upstream raw materials:

8-bromo-7-chloro-2-methoxy-1,5-naphthyridine

3-chloro-6-methoxy-[1,5]naphthyridine-4-carbonitrile

3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-carbonitrile

3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide

Downstream raw materials:

trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine