tert-Butyl adamantan-1-ylcarbamate

Base Information

• Chemical Name: tert-Butyl adamantan-1-ylcarbamate
• CAS No.: 151476-40-3
• Molecular Formula: C15H25 N O2
• Molecular Weight: 251.369
• European Community (EC) Number: 685-747-6
• DSSTox Substance ID: DTXSID60401099
• Nikkaji Number: J2.229.708B
• Wikidata: Q82204154
• Mol file: 151476-40-3.mol

Synonyms:151476-40-3;N-t-Boc-1-adamantylamine;tert-Butyl adamantan-1-ylcarbamate;tert-butyl N-(1-adamantyl)carbamate;1-(Boc-amino)adamantane;SCHEMBL136224;1-(Boc-amino)adamantane, 95%;DTXSID60401099;tert-Butyladamantan-1-ylcarbamate;AKOS002323767;FT-0663422;VU0493857-1;F79932;TERT-BUTYL N-(ADAMANTAN-1-YL)CARBAMATE;tert-butyl (3s,5s,7s)-adamantan-1-ylcarbamate;J-008810;F0035-0406;TERT-BUTYL N-[(3R,5S,7S)-ADAMANTAN-1-YL]CARBAMATE

Chemical Property of tert-Butyl adamantan-1-ylcarbamate

Chemical Property:

• Vapor Pressure: 4.16E-05mmHg at 25°C
• Melting Point: 110-115°C
• Refractive Index: 1.519
• Boiling Point: 351.3°C at 760 mmHg
• Flash Point: 166.2°C
• PSA: 38.33000
• Density: 1.07g/cm³
• LogP: 3.87080
• Storage Temp.: ?20°C
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 251.188529040
• Heavy Atom Count: 18
• Complexity: 315

Purity/Quality:

97% ^*data from raw suppliers

N-t-Boc-1-adamantylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC12CC3CC(C1)CC(C3)C2
• Uses: Intermediate for the preparation of Amantadine.

Technology Process of tert-Butyl adamantan-1-ylcarbamate

There total 7 articles about tert-Butyl adamantan-1-ylcarbamate 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: 90.0%

1-Adamantanecarboxylic acid (828-51-3) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyl adamantan-1-yl-carbamate (151476-40-3)

Guidance literature:

With sodium azide; tetrabutylammomium bromide; zinc trifluoromethanesulfonate; In tetrahydrofuran; at 40 ℃; for 24h;

DOI:10.1021/ol051428b

Reference yield: 75.0%

adamantane-1-carboxamide (5511-18-2) + bromo(t-butoxy)copper(II) → N-tert-butyl adamantan-1-yl-carbamate (151476-40-3)

Guidance literature:

In tetrahydrofuran; for 5h; Ambient temperature;

DOI:10.1246/cl.1993.1273

Reference yield: 55.0%

1-Azidoadamantane (24886-73-5) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyl adamantan-1-yl-carbamate (151476-40-3)

Guidance literature:

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; In methanol; at 20 ℃; for 3h; Sealed tube; Darkness;

DOI:10.1055/a-1579-2190

upstream raw materials:

adamantane-1-carboxamide

1-Adamantanecarboxylic acid

di-tert-butyl dicarbonate

1-Adamantanamine

Downstream raw materials:

N-(adamantan-1-yl)benzamide

N-(2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxycarbonyl)-1-adamantylamine

N-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxycarbonyl)-1-adamantylamine

N-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxycarbonyl)-1-adamantylamine

Refernces

• 1、 Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter. "Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions". supporting information. p. 133 - 146. Retrieved 2021/11/04.
• 2、 Lim, Diane S. W.,Lew, Tedrick T. S.,Zhang, Yugen. "Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates". supporting information. p. 6054 - 6057. Retrieved 2016/01/09.