170508-14-2

Basic information

• Product Name: Methyl 6-((tert-butoxycarbonyl)aMino)spiro[3.3]heptane-2-carboxylate
• Synonyms: Methyl 6-((tert-butoxycarbonyl)aMino)spiro[3.3]heptane-2-carboxylate;6-[(tert-Butoxycarbonyl)amino]spiro[3.3]-heptane-2-carboxylic acid methyl ester;Methyl 6-(Boc-aMino)spiro[3.3]heptane-2-carboxylate;6-[(tert-Butoxycarbonyl)amino]spiro[3.3]heptane-2-carboxylic acid methyl ester - B6144
• CAS NO: 170508-14-2
• Molecular Formula: C14H23NO4
• Molecular Weight: 269.33672
• Mol File: 170508-14-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 370.3±41.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• PKA: 12.29±0.40(Predicted)
• CAS DataBase Reference: Methyl 6-((tert-butoxycarbonyl)aMino)spiro[3.3]heptane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 6-((tert-butoxycarbonyl)aMino)spiro[3.3]heptane-2-carboxylate(170508-14-2)
• EPA Substance Registry System: Methyl 6-((tert-butoxycarbonyl)aMino)spiro[3.3]heptane-2-carboxylate(170508-14-2)

Safety Data

• Hazardous Substances Data: 170508-14-2(Hazardous Substances Data)

Usage

General Description

Methyl 6-((tert-butoxycarbonyl)amino)spiro[3.3]heptane-2-carboxylate is a chemical compound commonly used in organic synthesis. It is a spirocyclic compound with a tert-butoxycarbonyl-protected amino group. The presence of the spirocyclic ring in this compound makes it useful for the construction of complex organic molecules. It is often utilized in the pharmaceutical and agrochemical industries for the synthesis of biologically active compounds. Additionally, it may also find applications in material science and fine chemical production. Due to its versatile nature, this compound is of interest to researchers and chemists working in various fields of organic chemistry.

Upstream product

• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1808249-67-3 (racemic)-methyl 2-aminospiro[3.3]heptane-6-carboxylate hydrochloride 
• 10481-25-1 Methyl-hydrogen-spiro<3.3>heptan-2,6-dicarboxylat 
• 28345-63-3 (+/-)-2-carbomethoxyspiro<3.3>heptane-6-carboxamide 

Downstream Products

• 1087798-38-6 6-[(tert-butoxycarbonyl)amino]spiro[3.3]heptane-2-carboxylic acid 

Relevant articles and documents

BICYCLIC CARBOXAMIDES AND METHODS OF USE THEREOF

Compounds, compositions and methods are provided for modulating the activity of EP2 and EP4 receptors, and for the treatment, prevention and amelioration of one or more symptoms of diseases or disorders related to the activity of EP2 and EP4 receptors. In certain embodiments, the compounds are antagonists of both the EP2 and EP4 receptors.

(±)-N9-(2-(hydroxymethyl)spiro[3.3]hept-6-yl)adenine. The first biologically active saturated analogue of adenallene with axial dissymmetry

Synthesis of the title analogue 2 is described. Fecht's acid (3) was esterified with N,N-dimethylformamide dimethyl acetal to give monoester 4 along with diester 5. Compound 4 was transformed to ester amide 6 by the reaction with isobutyl chloroformate and triethylamine followed by ammonolysis. Hoffman rearrangement of 6 effected by lead tetraacetate in tert-butyl alcohol led to the N-tert-butoxycarbonyl ester 7. The latter was reduced with Ca(BH4)2 to give the protected amino alcohol 8. Removal of the N-tert-butoxycarbonyl group with 2 M HCl in methanol afforded the hydrochloride of amino alcohol 2. Reaction of 9 with 5-amino-4,6-dichloropyrimidine and triethylamine gave the pyrimidine derivative 10 which, in turn, was cyclized to 6-chloropurine 11a. Ammonolysis of the latter intermediate afforded the title analogue 2. The 1H NMR spectrnm of Fecht's acid (3) in CD3COCD3 showed that four methylene protons were magnetically nonequivalent (two quartets) whereas the other four were equivalent, forming a single doublet. Compound 2 inhibited the replication of human cytomegalovirus (IC50 32 μM) and growth of murine leukemia L1210 cells (IC50 30 μM). Zone assays showed inhibition of the following tumor cultures at 0.5 mg/disk: murine leukemia P388, mouse tumors PO3, C38, and M17/Adr as well as human tumors MCF-7 and CX-1.