151476-40-3

Usage

Chemical Properties

White Solid

Uses

Intermediate for the preparation of Amantadine.

InChI:InChI=1/C15H25NO2/c1-14(2,3)18-13(17)16-15-7-10-4-11(8-15)6-12(5-10)9-15/h10-12H,4-9H2,1-3H3,(H,16,17)

Upstream product

• 828-51-3 1-Adamantanecarboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 768-94-5 1-Adamantanamine 
• 1660-04-4 1-acetyladamantane 
• 768-95-6 1-adamanthanol 
• 24886-73-5 1-Azidoadamantane 
• 5511-18-2 adamantane-1-carboxamide 

Downstream Products

• 1332305-26-6 N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxycarbonyl)-1-adamantylamine 
• 1332305-34-6 N-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxycarbonyl)-1-adamantylamine 
• 1332305-32-4 N-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxycarbonyl)-1-adamantylamine 
• 1332305-36-8 N-(2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxycarbonyl)-1-adamantylamine 
• 19026-84-7 N-(adamantan-1-yl)benzamide 

Relevant academic research and scientific papers

Transformation of Primary Carboxamides to N-(t-Butoxycarbonyl)amines Using CuBr2-LiOBut

The reaction of primary carboxamides with the copper(II) reagent prepared from copper(II) bromide and lithium t-butoxide gave the corresponding N-(t-butoxycarbonyl)amines in good to high yields.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.

Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.

RADIATION-SENSITIVE RESIN COMPOSITION, METHOD FOR FORMING A RESIST PATTERN, COMPOUND, AND POLYMER

A radiation-sensitive resin composition includes a first polymer that includes a repeating unit having an acid-labile group and becomes alkali-soluble upon dissociation of the acid-labile group, and a radiation-sensitive acid-generating agent. The acid-labile group has a structure shown by a general formula (1). R1 represents a methyl group or the like, R2 represents a hydrocarbon group that forms a cyclic structure, R3 represents a fluorine atom or the like, R4 represents a carbon atom, and n1 is an integer from 1 to 7.

One-pot curtius rearrangement processes from carboxylic acids

An efficient and practical synthesis of amine derivatives from carboxylic acids is described using new one-pot Curtius rearrangement processes. The preparation of carbamate-protected amines and anilines, as well as ureas was achieved in good to excellent yields on a multigram scale. Georg Thieme Verlag Stuttgart.

Boc-protected amines via a mild and efficient one-pot curtius rearrangement

(Chemical Equation Presented) The reaction of a carboxylic acid with di-tert-butyl dicarbonate and sodium azide allowed the formation of an acyl azide intermediate, which undergoes a Curtius rearrangement in the presence of tetrabutylammonium bromide and zinc(II) triflate. The trapping of the isocyanate derivative in the reaction mixture led to the desired tert-butyl carbamate in high yields at low temperature. These reaction conditions are compatible with a variety of substrates, including malonate derivatives, which provide access to protected amino acids.