75885-59-5

Usage

Uses

2,2-Dimethylcyclopropylcarboxylic acid

InChI:InChI=1/C6H10O2/c1-6(2)3-4(6)5(7)8/h4H,3H2,1-2H3,(H,7,8)

Upstream product

• 854432-02-3 4-bromo-3,3-dimethyl-butyric acid ethyl ester 
• 5722-11-2 rac-2,2-dimethylcyclopropanecarbonitrile 
• 16783-11-2 ethyl (±)-2,2-dimethylcyclopropanecarboxylate 
• 1192-44-5 (+/-)-2-Brom-3.3-dimethyl-cyclobutanon 
• 932-58-1 l-methyl dl-2,2-dimethylcyclopropane-1-carboxylate 
• 33422-32-1 1,1-dimethyl-2-(2-methyl-1-propenyl)cyclopropane 
• 930-50-7 [(1RS)-2,2-dimethylcyclopropyl]methanol 
• 1192-33-2 3,3-dimethylcyclobutan-1-one 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 22308-12-9 1,3-bis((p-toluenesulfonyl)oxy)-2,2-dimethylpropane 
• 556-82-1 3-methyl-2-buten-1-ol 
• 31044-87-8 neopentyl glycol bis(benzenesulfonate) 
• 143-33-9 sodium cyanide 
• 3123-97-5 dihydro-5,5-dimethyl-2(3H)-furanone 

Downstream Products

• 932-58-1 l-methyl dl-2,2-dimethylcyclopropane-1-carboxylate 
• 50675-57-5 dl-2,2-dimethylcyclopropane-1-carboxylic acid chloride 
• 14590-53-5 (+)-1S-2,2-dimethylcyclopropane-carboxylic acid 
• 191476-68-3 2,2-Dimethyl-cyclopropanecarbothioic acid S-(2,4,6-trimethyl-phenyl) ester 
• 75885-58-4 (S)-2,2-dimethylcyclopropanecarboxamide 
• 85394-14-5 (+)-(Z)-2-(2,2-dimethylcyclopropanecarboxamido)-2-octenoic acid 
• 82009-34-5 cilastatine 
• 59671-39-5 1-(2,2-Dimethyl-cyclopropyl)-1-phenyl-ethanol 
• 61971-68-4 1-(2,2-Dimethyl-cyclopropyl)-1-(4-trifluoromethyl-phenyl)-ethanol 
• 61971-69-5 1-(3,5-Bis-trifluoromethyl-phenyl)-1-(2,2-dimethyl-cyclopropyl)-ethanol 
• 22308-12-9 1,3-bis((p-toluenesulfonyl)oxy)-2,2-dimethylpropane 
• 1374882-92-4 [(S)-1-((S)-2-{4-[4'-({6-[(R)-4-((S)-2,2-Dimethyl-cyclopropane-carbonyl)-2-methyl-piperazin-1-yl]-pyridine-3-carbonyl}-amino)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester 
• 1374883-86-9 [(S)-1-((S)-2-{4-[5'-Chloro-4'-({6-[(R)-4-((S)-2,2-dimethyl-cyclopropanecarbonyl)-2-methyl-piperazin-1-yl]-pyridine-3-carbonyl}-amino)-2'-trifluoromethyl-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester 
• 1428555-91-2 N-(2-aminophenyl)-2,2-dimethylcyclopropanecarboxamide 

Relevant academic research and scientific papers

Nitroxyl radical reactions with 4-pentenyl- and cyclopropylketenes: New routes to 5-hexenyl- and cyclopropylmethyl radicals

4-Pentenylketenes 4a and 9 and cyclopropylketenes 3a, 13, 14 (RCH=C=O) are generated by photochemical Wolff rearrangements and observed by IR as relatively long-lived species at room temperature in hydrocarbon solvents. The reactions of these ketenes with the nitroxyl radicals tetramethylpiperidinyloxyl (TEMPO, TO?) and tetramethylisoindoline-2-oxyl (TMIO, IO?) form carboxy substituted 5-hexenyl and cyclopropylmethyl radicals which are either trapped by a second nitroxyl radical or undergo rearrangements followed by trapping. The rate constant of the reaction of 4a with TEMPO was similar to that of n-BuCH=C=O (1b), while 3a was 4.3 times more reactive, indicating cyclopropyl stabilization of the incipient radical.

A new approach to the synthesis of cilastatin, an inhibitor of renal dipeptidase

A convenient preoarative synthesis of cilastatin, an inhibitor of renal dipeptidase used in drugs with the antibiotic imipenem, has been elaborated.The key intermediate in this synthesis is 2-amino-7-chloroheptanoic acid prepared by oxidative cleavage of cycloheptanone followed by bromination of 7-chloroheptanoyl chloride with subsequent amination of the 2-bromo-7-chloroheptanoic acid thus formed.All of the stages of the new synthesis are easily performed, as is the isolation of the intermediate products, and they do not require any organometallic reagents. - Key words: cilastatin, (R)-cysteine, 7-chloroheptanoic acid, 2-amino-7-chloro-2-heptenoic acid, 2,2-dimethylcyclopropanecarbonyl chloride; oxidation, bromination, amination, cyclopropanation.

Process for resolution of racemates of 2,2-dimethylcyclopropanecarboxylic acid

The enantiomers of 2,2-dimethylcyclopropanecarboxylic acid are separated by esterification with the hydroxy group of optically active mandelic acid methyl ester, crystallization of the diastereomeric esters and subsequent hydrolysis of the diastereomeric esters.

Menthyl 2,2-dimethylcyclopropanecarboxylate and resolution of the same

An ester obtained from 2,2-dimethylcyclopropanecarboxylic acid and optically active menthol, represented by the formula, STR1 is effectively resolved into diastereomers, which upon hydrolysis give optically active 2,2-dimethylcyclopropanecarboxylic acid.

Azetidines. 5. Reaction of 1,1,3,3-Tetramethyl- and 1-Benzyl-1,3,3-trimethylazetidinium Ions with Butyllithium and Phenyllithium. Deuterium Labeling as a Mechanistic Probe

The reactions of 1,1,3,3-tetramethylazetidinium iodide (1) and 1-benzyl-1,3,3-trimethylazetidinium bromide (7) with butyllithium and with phenyllithium were studied in ether.The products from the reaction of 1 with butyllithium were 1,3,3-trimethylpyrrolidine (2), 3,3-dimethyl-4-(methylamino)-1-butene (3), 1-(dimethylamino)-2,2-dimethylheptane (4), neopentylpyrrolidine (5), and 1-(dimethylamino)-2,2-dimethylcyclopropane (6).With phenyllithium, 1 gave 2 and 1-(dimethylamino)-2,2-dimethyl-3-phenylpropane (11).With butyllithium, 7 gave 2-phenyl-1,4,4-trimethylpyrrolidine (8), 1-benzyl-3,3-dimethylpyrrolidine (9), and 1-neopentyl-2-phenylpyrrolidine (10).The reaction of phenyllithium with 7 gave only 8 and 9.Mechanistic information was obtained by labeling 1 with deuterium in three different ways: N-methyl-d3, 2,2-d2, and N-methyl-d3-2,2-d2.A primary kinetic isotope effect of 9.4 was found for the formation of 2 from 1-N-methyl-d3.When 2 was formed from 1-2,2-d2, a secondary kinetic isotope effect of 1.17 was measured.The formation of 4 from 1-2,2-d2 was accompanied by a primary kinetic isotope effect of 4.7, suggesting a carbene intermediate.Ylide carbanions involving decomposition to a carbene carbanion in the formation of 3 and an azomethine ylide in the formation of 5 and 9 are probable intermediates.It is postulated that the azomethine ylides react with ethylene formed from the reaction of butyllithium with the solvent ether by means of a concerted (4 + 2) cycloaddition reaction.A primary kinetic isotope effect of 20 was found for the formation of pentylbenzene from dibenzyldimethylammonium bromide and butyllithium.