N-(3-endo)-9-Azabicyclo[3.3.1]non-3-ylcarbamic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: N-(3-endo)-9-Azabicyclo[3.3.1]non-3-ylcarbamic acid 1,1-dimethylethyl ester
• CAS No.: 155560-04-6
• Molecular Formula: C13H24N2O2
• Molecular Weight: 240.34200
• Mol file: 155560-04-6.mol

Synonyms:N-(3-ENDO)-9-AZABICYCLO[3.3.1]NON-3-YLCARBAMIC ACID 1,1-DIMETHYLETHYL ESTER;endo-tert-Butyl 9-azabicyclo[3.3.1]nonan-3-ylcarbamate;tert-butyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate;tert-butyl 9-azabicyclo[3.3.1]nonan-3-ylcarbamate;PBY2010319;ENDO-3-(BOC-AMINO)-9-AZABICYCLO[3.3.1]NONANE;

Chemical Property of N-(3-endo)-9-Azabicyclo[3.3.1]non-3-ylcarbamic acid 1,1-dimethylethyl ester

Chemical Property:

• PSA: 50.36000
• LogP: 2.90390
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

97% ^*data from raw suppliers

endo-3-(Boc-amino)-9-azabicyclo[3.3.1]nonane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(3-endo)-9-Azabicyclo[3.3.1]non-3-ylcarbamic acid 1,1-dimethylethyl ester

There total 6 articles about N-(3-endo)-9-Azabicyclo[3.3.1]non-3-ylcarbamic acid 1,1-dimethylethyl 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: 89.0%

tert-butyl 9-methyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate (1006601-11-1) → tert-butyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate (155560-04-6,1208530-70-4,599165-35-2)

Guidance literature:

With sodium hydroxide; potassium permanganate; water; In tetrahydrofuran; at 0 - 20 ℃;

Reference yield:

3α-<(tert-butyloxycarbonyl)amino>-9-benzyl-9-azabicyclo<3.3.1>nonane → tert-butyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate (155560-04-6,1208530-70-4,599165-35-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In ethanol; ethyl acetate; at 40 - 50 ℃; under 760.051 Torr;

DOI:10.1039/c3ob40489g

Reference yield:

9-benzyl-3-oxo-9-azoniabicyclo[3.3.1]nonane bromide → tert-butyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate (155560-04-6,1208530-70-4,599165-35-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydroxylamine hydrochloride; sodium hydroxide / water; ethanol / 14 h / Reflux; Inert atmosphere

2.1: sodium tetrahydroborate; nickel dichloride / methanol / 1.5 h / -20 - 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

4.1: hydrogen; acetic acid; palladium 10% on activated carbon / ethyl acetate; ethanol / 40 - 50 °C / 760.05 Torr

With sodium tetrahydroborate; palladium 10% on activated carbon; hydroxylamine hydrochloride; hydrogen; acetic acid; triethylamine; sodium hydroxide; nickel dichloride; In methanol; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1039/c3ob40489g

upstream raw materials:

tert-butyl 9-methyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate

Glutaraldehyde

(±)-(1R,3r,5S)-9-benzyl-9-azabicyclo[3.3.1]nonan-3-yl acetate

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