6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine

Base Information

• Chemical Name: 6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine
• CAS No.: 855301-94-9
• Molecular Formula: C₁₇H₂₂N₂O
• Molecular Weight: 270.374
• Mol file: 855301-94-9.mol

Synonyms:6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine

Chemical Property of 6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine

There total 2 articles about 6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine 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:

2H-Hexahydro-2-(3-chloropropyl)-2-cyano-6-phenyloxazolo<3,2-a>pyridne (855301-93-8) → 6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine (855301-94-9)

Guidance literature:

With naphthalene; lithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tetlet.2005.04.019

Reference yield:

(-)-2-cyano-6-phenyloxazolopiperidine (88056-92-2) → 6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine (855301-94-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di-isopropylamine; n-BuLi / tetrahydrofuran / -78 °C

1.2: tetrahydrofuran

2.1: lithium; naphthalene / tetrahydrofuran / 0.33 h / -78 °C

With n-butyllithium; naphthalene; lithium; diisopropylamine; In tetrahydrofuran;

DOI:10.1021/jo050258d

Reference yield: 18.0%

6-phenyl-2,3,5,6,9,10-hexahydro-1H-4-oxa-6a-azacyclopenta[d]naphthalen-3a-ylamine (855301-94-9) + 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene (42201-84-3) → C17H21NO2 (855310-69-9) + ((3aS,6R,7S,10aR)-3a-Hydroxy-6-phenyl-decahydro-4-oxa-6a-aza-cyclopenta[d]naphthalen-7-yl)-acetic acid methyl ester

Guidance literature:

With ytterbium trifluoromethanesulfonate; water; In tetrahydrofuran; Heating;

DOI:10.1016/j.tetlet.2005.04.019

upstream raw materials:

2H-Hexahydro-2-(3-chloropropyl)-2-cyano-6-phenyloxazolo<3,2-a>pyridne

(-)-2-cyano-6-phenyloxazolopiperidine

Downstream raw materials:

C₁₇H₂₁NO₂

3a-amino-6-phenyldecahydro-4-oxa-6a-azacyclopenta[d]naphthalene-7-carbonitrile

3a-hydroxy-6-phenyldecahydro-4-oxa-6a-azacyclopenta[d]naphthalene-7-carbonitrile

C₁₉H₂₂N₂O