(+)-N-Acetyl 3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-β][1,4]oxazine-9-ol Triisopropylsilyl Ether

Base Information

• Chemical Name: (+)-N-Acetyl 3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-β][1,4]oxazine-9-ol Triisopropylsilyl Ether
• CAS No.: 1034706-81-4
• Molecular Formula: C23H37NO3Si
• Molecular Weight: 403.637
• Mol file: 1034706-81-4.mol

Synonyms:(+)-N-Acetyl 3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-β][1,4]oxazine-9-ol Triisopropylsilyl Ether;

Chemical Property of (+)-N-Acetyl 3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-β][1,4]oxazine-9-ol Triisopropylsilyl Ether

Chemical Property:

• Boiling Point: 486.718 °C at 760 mmHg
• Flash Point: 248.159 °C
• PSA: 38.77000
• Density: 1.023 g/cm³
• LogP: 5.41340
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

99% ^*data from raw suppliers

(+)-N-Acetyl3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-olTriisopropylsilylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: PHNO precursor. (+)-N-Acetyl 3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-β][1,4]oxazine-9-ol Triisopropylsilyl Ether is used for the preparation of radiolabeled amines, which are useful in Positron Emission Tomog. (PET) and Single Photon Emission Computed Tomog. (SPECT), and hence, can be utilized for imaging neuro-receptors with radiolabeled agonists.

Technology Process of (+)-N-Acetyl 3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-β][1,4]oxazine-9-ol Triisopropylsilyl Ether

There total 13 articles about (+)-N-Acetyl 3,4,4a,5,6,10b-Hexahydro-2H-naphtho[1,2-β][1,4]oxazine-9-ol Triisopropylsilyl Ether 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%

(+)-trans-9-triisopropylsilyloxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2b][1,4]oxazine (1535196-90-7) + acetic anhydride (108-24-7) → (+)-N-acetyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-ol triisopropylsilyl ether (1034706-81-4)

Guidance literature:

With pyridine; at 0 - 25 ℃; for 3h;

DOI:10.1016/j.tetlet.2013.11.113

Reference yield:

7-hydroxy-1-tetralone (22009-38-7) → (+)-N-acetyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-ol triisopropylsilyl ether (1034706-81-4)

Guidance literature:

Multi-step reaction with 12 steps

1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

2: hydroxylamine hydrochloride; pyridine / 16 h / 120 °C

3: pyridine / 16 h / 20 °C

4: potassium ethoxide / ethanol; benzene / 5 h / 0 °C / Inert atmosphere

5: sodium tetrahydroborate / methanol / 3 h / 20 °C

6: sodium hydroxide / dichloromethane / 3 h / 0 - 20 °C

7: sodium hydride / tetrahydrofuran; acetonitrile; mineral oil

8: lithium aluminium tetrahydride / 5 °C / Reflux

9: 5%-palladium/activated carbon; hydrogen / methanol / 16 h

10: CHIRALPAK AD-H column / Resolution of racemate

11: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C

12: pyridine / 3 h / 0 - 25 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 5%-palladium/activated carbon; hydroxylamine hydrochloride; potassium ethoxide; hydrogen; sodium hydride; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil; benzene;

DOI:10.1016/j.tetlet.2013.11.113

Reference yield:

trans-9-hydroxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2b][1,4]oxazine (92422-30-5) → (+)-N-acetyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-ol triisopropylsilyl ether (1034706-81-4)

Guidance literature:

Multi-step reaction with 3 steps

1: CHIRALPAK AD-H column / Resolution of racemate

2: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C

3: pyridine / 3 h / 0 - 25 °C

With pyridine; 1H-imidazole; In dichloromethane;

DOI:10.1016/j.tetlet.2013.11.113

upstream raw materials:

trans-9-hydroxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2b][1,4]oxazine

(+)-trans-9-triisopropylsilyloxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2b][1,4]oxazine

acetic anhydride

7-Methoxy-1-tetralone