62087-82-5

Usage

Purification Methods

Dissolve it in n-hexane (ca 10g in 150 mL) and keep at 0o for 24hours. Any 1-adamantanol present will separate. Filter and evaporate to dryness. The crystalline residue has m 31-32o and is recrystallised from n-hexane (90g/500mL), (IR (KBr):  max 1242, 1824 and 2340 cm-1). There should be no OH str band above 2500 cm-1. [Moroder et al. Hoppe-Seyler’s Z Physiol Chem 357 1647 1976, cf Haas et al. J Am Chem Soc 88 1988 1966.]

InChI:InChI=1/C11H15FO2/c12-10(13)14-11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2

Upstream product

• 101681-00-9 1-Chloroethyl 1-Adamantyl Carbonate 
• 75-69-4 trichlorofluoromethane 
• 768-95-6 1-adamanthanol 

Downstream Products

• 130258-35-4 [Acetyl-(adamantan-1-yloxycarbonyl)-amino]-acetic acid benzyl ester 
• 130258-29-6 Acetyl-phenyl-carbamic acid adamantan-1-yl ester 
• 65815-75-0 Carbonic acid diadamantan-1-yl ester 
• 207510-25-6 Pyrrole-1,3-dicarboxylic acid 1-adamantan-1-yl ester 3-cyclohexyl ester 
• 768-92-3 1-adamantyl fluoride 
• 768-95-6 1-adamanthanol 
• 74975-65-8 1-adamantyl 2,2,2-trifluoroethyl ether 
• 6221-75-6 1-Adamantyl ethyl ether 
• 37994-87-9 1-Adamantyl ethyl carbonate 
• 6221-74-5 1-methoxyadamantane 
• 37994-86-8 adamantan-1-yl methyl carbonate 
• 56125-84-9 1-adamantyl-isopropyl ether 
• 37994-88-0 C₁₄H₂₂O₃ 
• 76500-90-8 1-(2,2,2-Trifluoro-1-trifluoromethyl-ethoxy)-adamantane 

Relevant academic research and scientific papers

Process for preparing aliphatic fluorofomates

A method for the production of aliphatic fluoroformates, wherein carbonyl fluoride is made to react with aliphatic alcohol in the presence of sodium fluoride in ether at a temperature of ?20° to 50° C. The method is carried out using carbonyl fluoride obtained by reacting phosgene with surplus powdered sodium fluoride, whereby the grains thereof have a specific surface of 0.1 m2/g or more and/or an average diameter of 20 μm or less, at a temperature ranging from 25° to 120° C. The method enables unstable fluoroformates such as tertiobutyl to be obtained with excellent yields.

A Simple Conversion of 1-Chloroethyl Carbonates to Fluoroformates: Value in the Preparation of Tertiary Alkyl Fluoroformates

When the economical and easily available 1-chloroalkyl carbonates (RCHClOCO2R') are heated neat or in solution with KF in the pesence of 18-crown-6 catalyst, they fragment to aldehydes (RCHO) and fluoroformates (FCO2R').If the system is evacuated during reaction and either or both products are removed as formed, then the process is driven to completion and fluoroformates are isolated in good yield.The new methodology (which exemplifies an unusual conversion of an ester to an acid halide) is especially valuable in the synthesis of important tertiary alkyl fluoroformates and benzyl fluoroformate (with R as CH3 in the carbonate): tert-butyl fluoroformate (BOC-F, 84percent yield), tert-amyl fluoroformate (83percent), 1-adamantyl fluoroformate (76percent), benzyl fluoroformate (60percent).Boc-F previously has been recommended as a superior reagent for the preparation of Boc-amino acids, but earlier routes to this reagent have been expensive and impractical.When R in the carbonate reactant is Cl3C, the reaction proceeds cleanly without the 18-crown-6 catalyst (Boc-F in 79percent yield).This latter variation is most useful on a small industrial scale.

Process for the preparation of fluoroformates

A process for the preparation of fluoroformates of formula: STR1 in which R1 is a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or polycyclic radical, or substituted or unsubstituted araliphatic radical or an aromatic radical, which consists of reacting a carbonate of formula: STR2 in which R1 has the same meaning as hereinabove and R2 is hydrogen, alkyl of 1-12 carbon atoms, cycloalkyl of 5-12 carbon atoms, saturated or unsaturated, unsubstituted or substituted by one or more halogen atoms or R2 is aryl, unsubstituted or substituted by one or more halogen atoms, with an alkali or alkaline earth fluoride, ammonium fluoride or a quaternary ammonium fluoride, of formula FNR3 R4 R5 R6, wherein R3, R4, R5, R6 are the same or different and are hydrogen, alkyl or aralkyl of 1-12 carbon atoms or a fluoride which is KHF2, NH4 HF2 or KSO2 F. The fluoride is activated by a complexing agent for the cation which is a cryptate, a cyclic or linear polyether or by means of a polar aprotic compound. The carbonate is split to give a reaction mixture containing an aldehyde and the fluoroformate which is removed from the reaction mixture.

1-Adamanty fluoroformate, a useful reagent in peptide chemistry (author's transl)

1-Adamantyl fluoroformate was prepared from 1-adamantol and fluorophosgene. The cristalline and stable fluoroformate was allowed to react with amino acids to give the corresponding 1-adamantyloxycarbonyl derivatives in consistently high yields. Additonally this new reagent proved to be ideally reactive for acylation of the imidazol function of histidine and histidyl-peptides.