2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

Base Information

• Chemical Name: 2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
• CAS No.: 81310-22-7
• Molecular Formula: C₉H₁₃NO₃*C₁₃H₂₄N₂
• Molecular Weight: 391.554
• Mol file: 81310-22-7.mol

Synonyms:

Chemical Property of 2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

There total 12 articles about 2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 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: 88.0%

(2R,5R)-3,3-Dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (81310-20-5) + 1,2,3,4,4a,5,6,7-octahydro-2,2,4a,7,7-pentametyl-1,8-naphthyridene (69340-58-5,308280-56-0,1212823-64-7) → 2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (81310-22-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 0.166667h; Ambient temperature;

DOI:10.1016/S0040-4039(01)82981-6

Reference yield:

3,3-dimethylpent-4-enoic acid (7796-73-8) → 2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (81310-22-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) SOCl₂ / 1.) reflux 2.) -78 deg C, THF

2: 90 percent / NH₂OH_.HCl / pyridine / 50 °C

3: 1.) Na 2.) HCl / 1.) i-PrOH, reflux 2.) Room temp.

4: 55 percent / mesitylmagnesium bromide / CH₂Cl₂ / Ambient temperature

5: 1.) N,N-diisopropylethylamine 2.) O₃ / 1.) DMF, 0 deg C 2.) Me OH, -30 deg C, Me₂S, R_.T_.

6: 85 percent / various solvent(s)

7: 72 percent / Ac₂O / pyridine / Ambient temperature

8: HCl / methanol / 0 °C

9: 62 percent / 3,36,9,9-pentamethyl-2,10-diaza-bicyclo-4.4.o>-1-decene, O₃ / methanol / -60 °C

10: O₂, NaHCO₃ / Pt / H₂O; acetone / 5 h / Ambient temperature

11: dimethylformamide / 3 h / Ambient temperature

12: 88 percent / H₂ / 10percent Pd-C / tetrahydrofuran / 0.17 h / Ambient temperature

With hydrogenchloride; thionyl chloride; hydroxylamine hydrochloride; hydrogen; oxygen; sodium; acetic anhydride; sodium hydrogencarbonate; ozone; N-ethyl-N,N-diisopropylamine; 1,2,3,4,4a,5,6,7-octahydro-2,2,4a,7,7-pentametyl-1,8-naphthyridene; 2-mesitylmagnesium bromide; hydrogenchloride; palladium on activated charcoal; platinum; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(01)82981-6

Reference yield:

4-(2,2-Dimethyl-but-3-enyl)-azetidin-2-one (81310-14-7) → 2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (81310-22-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) N,N-diisopropylethylamine 2.) O₃ / 1.) DMF, 0 deg C 2.) Me OH, -30 deg C, Me₂S, R_.T_.

2: 85 percent / various solvent(s)

3: 72 percent / Ac₂O / pyridine / Ambient temperature

4: HCl / methanol / 0 °C

5: 62 percent / 3,36,9,9-pentamethyl-2,10-diaza-bicyclo-4.4.o>-1-decene, O₃ / methanol / -60 °C

6: O₂, NaHCO₃ / Pt / H₂O; acetone / 5 h / Ambient temperature

7: dimethylformamide / 3 h / Ambient temperature

8: 88 percent / H₂ / 10percent Pd-C / tetrahydrofuran / 0.17 h / Ambient temperature

With hydrogen; oxygen; acetic anhydride; sodium hydrogencarbonate; ozone; N-ethyl-N,N-diisopropylamine; 1,2,3,4,4a,5,6,7-octahydro-2,2,4a,7,7-pentametyl-1,8-naphthyridene; hydrogenchloride; palladium on activated charcoal; platinum; In tetrahydrofuran; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(01)82981-6

upstream raw materials:

(2R,5R)-3,3-Dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

1,2,3,4,4a,5,6,7-octahydro-2,2,4a,7,7-pentametyl-1,8-naphthyridene

3,3-dimethylpent-4-enoic acid

4-(2,2-Dimethyl-but-3-enyl)-azetidin-2-one