4942-47-6

Basic information

• Product Name: 1-Adamantaneacetic acid
• Synonyms: a-(1-Adamantyl)acetic acid;Adamantane-1-acetic acid;1-adamantylacetic acid(SALTDATA: FREE);(Adamant-1-yl)acetic acid;2-(adaMantan-1-yl)acetic acid;1-AdaMantaneacetic acid, 98% 10GR;1-AdaMantaneacetic acid, 98.5%;1-AdaMaMntaneacetic acid
• CAS NO: 4942-47-6
• Molecular Formula: C₁₂H₁₈O₂
• Molecular Weight: 194.27
• EINECS: 225-585-1
• Product Categories: Adamantanes;cyclic compounds;Adamantane derivatives
• Mol File: 4942-47-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 134-137 °C(lit.)
• Boiling Point: 270.73°C (rough estimate)
• Flash Point: 163 °C
• Appearance: White to off-white/Crystalline Powder or Crystals
• Density: 1.0086 (rough estimate)
• Vapor Pressure: 7.23E-05mmHg at 25°C
• Refractive Index: 1.4949 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Solubility in Methanol - almost transparency
• PKA: 5.00±0.10(Predicted)
• BRN: 641412
• CAS DataBase Reference: 1-Adamantaneacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Adamantaneacetic acid(4942-47-6)
• EPA Substance Registry System: 1-Adamantaneacetic acid(4942-47-6)

Safety Data

• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-15-10
• Safety Statements: 22-24/25-43-7/8
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 4942-47-6(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder or crystals

Uses

1-Adamantaneacetic acid was used as an acylating agent in determining pharmacological characteristics of ten new analogues of bradykinin (Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg) that were modified in the N-terminal part of the molecule.

Biochem/physiol Actions

1-Adamantaneacetic acid is an inhibitor of chorismate mutase-prephenate dehydrogenase (EC 1.3.1.12) from Escherichia coli K12 (strain JP 232).

Purification Methods

Dissolve the acid in hot NaOH, treat with charcoal, filter and acidify. Collect the solid, wash it with H2O, dry and recrystallise it from MeOH. [Stetter et al. Chem Ber 92 1629 1959.] The acid chloride [2094-72-6] has M 168.7, m 51-54o, and b 135-136o/1mm. LACHRYMATORY.

InChI:InChI=1/C12H18O2/c13-11(14)7-12-4-8-1-9(5-12)3-10(2-8)6-12/h8-10H,1-7H2,(H,13,14)/p-1

Synthetic route

2-(1-adamantyl)-1-nitro-1-(pyridine-thiyl)ethane (104543-11-5) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With dihydrogen peroxide; potassium carbonate In tetrahydrofuran; methanol at 40℃; for 15h;	95%

1-Adamantyl bromide (768-90-1) + 1,1-Dichloroethylene (75-35-4) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 2℃; for 2.5h;	93%
(i) H2SO4, BF3, (ii) aq. H2SO4; Multistep reaction;
With sulfuric acid; boron trifluoride

Phosphoric acid 2-adamantan-1-yl-1-benzenesulfonyl-1-(pyridin-2-ylsulfanyl)-ethyl ester dimethyl ester → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium hydroxide	93%
With potassium hydroxide In methanol Yield given;

methyl 2-(adamantan-1-yl)acetate (27174-71-6) + sodium hydrogencarbonate (144-55-8) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In methanol	93%

Trifluoro-acetic acid 2-adamantan-1-yl-1-cyano-1-(pyridin-2-ylsulfanyl)-ethyl ester (144499-21-8) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium carbonate In water for 2h;	91%
With potassium carbonate In acetone at 25℃; for 12h; Yield given;

Acetic acid 1-cyano-2-(octahydro-2,5-methano-inden-3a-yl)-1-(pyridin-2-ylsulfanyl)-ethyl ester → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium carbonate In water	87%

ethyl 4-(adamant-1-yl)-phenyl acetate (15782-66-8) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With water; sodium hydroxide In methanol at 20℃; for 1h;	86%

Phosphoric acid 2-adamantan-1-yl-1-cyano-1-(pyridin-2-ylsulfanyl)-ethyl ester dimethyl ester (144499-22-9) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium hydroxide	85%

1,1-Dichloroethylene (75-35-4) + 1-nitroxyadamantane (32314-61-7) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With sulfuric acid at 5 - 15℃; for 1h;	80.6%

(3r,5r,7r)-1-(2,2-dibromovinyl)adamantane → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
Stage #1: (3r,5r,7r)-1-(2,2-dibromovinyl)adamantane With n-butyllithium In tetrahydrofuran at 0℃; for 1.5h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h;	77%

adamantylacetic acid acid 2-oxo-1,2,2-triphenylethyl ester (925681-80-7) → 13-oxa-indeno[1,2-l]phenanthrene (201-68-3) + (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With air In ethanol; acetonitrile Irradiation;	A n/a B 74%

methyl 2-(adamantan-1-yl)acetate (27174-71-6) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With bis(tri-n-butyltin)oxide In toluene for 72h; Heating;	25%

diazomethane (186581-53-3, 908094-01-9) + 1-Adamantanecarbonyl chloride (2094-72-6) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With diethyl ether Erwaermen des Reaktionsprodukts mit Ag2O, Na2CO3 und Na2S2O3 in wss. Dioxan;

1,1-Dichloroethylene (75-35-4) + adamantane (281-23-2) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With sulfuric acid; boron trifluoride diethyl etherate; tert-butyl alcohol

1,1-Dichloroethylene (75-35-4) + 1-adamanthanol (768-95-6) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
(i) BF3, H2SO4, (ii) aq. H2SO4; Multistep reaction;
With sulfuric acid; boron trifluoride

1-Carboxymethyladamantane nitrile (16269-13-9) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium hydroxide In ethylene glycol at 150℃;

adamantan-1-ylacetaldehyde (18220-83-2) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium permanganate In acetone

1,1-Dichloroethylene (75-35-4) + adamantane (281-23-2) → 1,3-adamantane diacetic acid (17768-28-4) + 2-(3-hydroxyadamantan-1-yl)acetic acid (17768-36-4) + (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With sulfuric acid; nitric acid In hexane at 25℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With sulfuric acid; nitric acid In hexane at 25℃; Yield given. Yields of byproduct given;
With sulfuric acid; nitric acid In hexane at 25℃; for 4.5h; Product distribution; Mechanism; var. reagent partners concentrations, temp., and solvents; also 1,3-dimethyladamantane;

2-acetoxyacrylonitrile (3061-65-2) + 1-Adamantanecarboxylic acid (828-51-3) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With 1-hydroxy-2(1H)-pyridinethione; potassium carbonate; dicyclohexyl-carbodiimide multistep reaction, other acids, other olefins (homologation of carboxylic acids);

2-(2-Adamantan-1-yl-1-benzenesulfonyl-1-trimethylsilanyl-ethanesulfinyl)-pyridine (135967-17-8) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium carbonate; trifluoroacetic acid 2) MeCN, H2O; Multistep reaction;

3-Adamantan-1-yl-2-(pyridine-2-sulfinyl)-propionitrile (163976-43-0) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium carbonate; trifluoroacetic anhydride 2) EtOH; Multistep reaction;
With potassium carbonate; trifluoroacetic anhydride 2.) acetonitrile; Yield given. Multistep reaction;

Acetic acid 2-adamantan-1-yl-1-cyano-1-(pyridin-2-ylsulfanyl)-ethyl ester (144499-23-0) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium carbonate In acetone at 25℃; for 12h; Yield given;

1-(bromomethyl)adamantane (14651-42-4) + carbon dioxide (124-38-9) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction;

Methanesulfonic acid 2-adamantan-1-yl-1-cyano-1-(pyridin-2-ylsulfanyl)-ethyl ester → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium carbonate In water

2-(2-Adamantan-1-yl-1-benzenesulfonyl-ethanesulfinyl)-pyridine → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With potassium carbonate; trifluoroacetic anhydride 1.) CH2Cl2, 2 h, room temp.; 2.) H2O, acetone, overnight at room temp.; Yield given. Multistep reaction;

methyl [2-(1-adamantylacetyl)-3-(1-adamantylmethylcarbonyloxy)-3-methoxy]-2-propenoate → 1-(1-adamantyl)propan-2-one (19835-39-3) + (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
With sulfuric acid; water

1-adamantylacetyl chloride (19835-38-2) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / NaOH / toluene / 1 h / 20 °C 2: H2SO4; water View Scheme

1-Adamantanecarboxylic acid (828-51-3) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: DCC / CH2Cl2 2: 33 percent Spectr. / CH2Cl2 / 0 - 5 °C / Irradiation 3: aq.K2CO3 / acetone / 12 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: DCC / CH2Cl2 2: 79 percent Spectr. / CH2Cl2 / 0 - 5 °C / Irradiation 3: aq.K2CO3 / acetone / 12 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1: DCC / CH2Cl2 2: 87 percent Spectr. / CH2Cl2 / 0 - 5 °C / Irradiation 3: MCPBA 4: 1) (CF3CO)2O, 2) aq.K2CO3 / 2) EtOH View Scheme

1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione (91233-19-1) → (adamant-1-yl)-acetic acid (4942-47-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 33 percent Spectr. / CH2Cl2 / 0 - 5 °C / Irradiation 2: aq.K2CO3 / acetone / 12 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: 79 percent Spectr. / CH2Cl2 / 0 - 5 °C / Irradiation 2: aq.K2CO3 / acetone / 12 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: 87 percent Spectr. / CH2Cl2 / 0 - 5 °C / Irradiation 2: MCPBA 3: 1) (CF3CO)2O, 2) aq.K2CO3 / 2) EtOH View Scheme
Multi-step reaction with 3 steps 1: 75 percent Spectr. / CH2Cl2 / 0 - 5 °C 2: m-chloroperbenzoic acid 3: 1) CF3CO2H 2) K2CO3 / 2) MeCN, H2O View Scheme
Multi-step reaction with 2 steps 1: 61 percent Spectr. / CH2Cl2 / 0 - 5 °C 2: 1M KOH / methanol View Scheme

methanol (67-56-1) + (adamant-1-yl)-acetic acid (4942-47-6) → methyl 2-(adamantan-1-yl)acetate (27174-71-6)

Conditions	Yield
With hydrogenchloride for 1h; Heating;	100%
With sulfuric acid Heating;	80%
With toluene-4-sulfonic acid
With sulfuric acid for 10h; Reflux;

1,3-dipropyl-5,6-diaminouracil (81250-34-2) + (adamant-1-yl)-acetic acid (4942-47-6) → 6-amino-1,3-dipropyl-5-<<(1-adamantyl)acetyl>amino>uracil (136199-23-0)

Conditions	Yield
With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,4-dioxane for 2h; Ambient temperature;	100%

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) + (adamant-1-yl)-acetic acid (4942-47-6) → (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester (87113-91-5)

Conditions	Yield
With N-Ethylmaleimide; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran	100%

(adamant-1-yl)-acetic acid (4942-47-6) → 2-(adamant-1-yl)ethanol (6240-11-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18h;	100%
With borane-THF In tetrahydrofuran at 5 - 10℃;	97%
Stage #1: (adamant-1-yl)-acetic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: With Glauber's salt In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	97%

(adamant-1-yl)-acetic acid (4942-47-6) → 1-adamantylacetyl chloride (19835-38-2)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 18h;	100%
With thionyl chloride; N,N-dimethyl-formamide In ethyl acetate at 20℃; for 3h;	99%
With thionyl chloride for 5h; Inert atmosphere; Reflux;	99%

methyl 6-aminocaproate hydrochloride (1926-80-3) + (adamant-1-yl)-acetic acid (4942-47-6) → Ada-Ahx-OMe (273201-95-9)

Conditions	Yield
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Inert atmosphere;	100%

C32H41N7O2 + (adamant-1-yl)-acetic acid (4942-47-6) + trifluoroacetic acid (76-05-1) → 6-(6-(4-(2-(2-(adamantan-1-yl)acetamido)ethyl)piperazin-1-yl)pyridin-3-yl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxamide 2,2,2-trifluoroacetate

Conditions	Yield
Stage #1: C32H41N7O2; (adamant-1-yl)-acetic acid With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethylsulfoxide-d6 at 20℃; Stage #2: trifluoroacetic acid In methanol; water	100%

C67H100O16Si2 + (adamant-1-yl)-acetic acid (4942-47-6) → C79H116O17Si2

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 20h; Inert atmosphere;	100%

1-[5-(benzyloxy)pyridin-2-yl]piperazine (823197-35-9) + (adamant-1-yl)-acetic acid (4942-47-6) → C28H35N3O2

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3.5h;	100%

(adamant-1-yl)-acetic acid (4942-47-6) + 2-(2-Aminoethoxy)ethanol (929-06-6) → C16H27NO3

Conditions	Yield
With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane	99%

methyl (L)-leucinate hydrochloride (7517-19-3) + (adamant-1-yl)-acetic acid (4942-47-6) → N-(1-adamantylacetyl)-L-leucine methyl ester (1040215-19-7)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	98%

2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8) + tert-butylisonitrile (119072-55-8, 7188-38-7) + (adamant-1-yl)-acetic acid (4942-47-6) → adamantan-1-ylacetic acid 1-tert-butylcarbamoyl-2,2,4,4-tetramethyl-3-oxocyclobutyl ester (1141681-57-3)

Conditions	Yield
In water at 20℃; for 72h; Passerini reaction;	98%

2-[2-[[(1,1-dimethylethyl)-dimethylsilyl]oxy]ethoxy]ethanol (131326-39-1) + (adamant-1-yl)-acetic acid (4942-47-6) → C22H40O4Si

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	98%

C27H37N5O3 + (adamant-1-yl)-acetic acid (4942-47-6) + trifluoroacetic acid (76-05-1) → 1-((S)-1-(1-(2-(2-(adamantan-1-yl)acetamido)ethyl)piperidin-4-yl)ethyl)-N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1H-indole-3-carboxamide 2,2,2-trifluoroacetate

Conditions	Yield
Stage #1: C27H37N5O3; (adamant-1-yl)-acetic acid With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethylsulfoxide-d6 at 20℃; Stage #2: trifluoroacetic acid In methanol; water	98%

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) + (adamant-1-yl)-acetic acid (4942-47-6) → 3'-O-adamantaneacetyl-5'-O-(4-4'-dimethoxytrityl)thymidine

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Molecular sieve;	97%

2-(2-tert-butyloxycarbonylaminoethoxy)ethanol (139115-91-6) + (adamant-1-yl)-acetic acid (4942-47-6) → 2-(2-((tert-butoxycarbonyl)amino)ethoxy)ethyl 2-(adamantan-1-yl)acetate

Conditions	Yield
Stage #1: 2-(2-tert-butyloxycarbonylaminoethoxy)ethanol; (adamant-1-yl)-acetic acid With dmap In dichloromethane at 20℃; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	97%
With dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	97%
In dichloromethane at 0 - 20℃;	97%
With benzotriazol-1-ol; 1,2-dichloro-ethane In dichloromethane

3-<(tert-butyldimethylsilyl)oxy>-4-methoxybenzyl alkohol (97315-19-0) + (adamant-1-yl)-acetic acid (4942-47-6) → 3-[tert-butyl(dimethyl)silyloxy]-4-methoxybenzyl adamantan-1-ylacetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	96%

1,1-Dichloroethylene (75-35-4) + (adamant-1-yl)-acetic acid (4942-47-6) → 1,3-adamantane diacetic acid (17768-28-4)

Conditions	Yield
With sulfuric acid; nitric acid for 5h; Ambient temperature;	95%

(adamant-1-yl)-acetic acid (4942-47-6) → (3-bromo-1-adamantyl)acetic acid (17768-34-2)

Conditions	Yield
With water; bromine for 1.5h; Heating;	94%
With bromine
With sulfuric acid; hydrogen bromide
With bromine In tetrachloromethane
With t-butyl bromide; sulfuric acid In tetrachloromethane at 10 - 20℃; for 2h;

(adamant-1-yl)-acetic acid (4942-47-6) + acetonitrile (75-05-8) → ((1R,3R,7R)-3-Acetylamino-adamantan-1-yl)-acetic acid

Conditions	Yield
With water; bromine 1.) reflux, 15 min, 2.) room temp., overnight;	94%

(adamant-1-yl)-acetic acid (4942-47-6) → C12H18OS

Conditions	Yield
Stage #1: (adamant-1-yl)-acetic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium hydrogen sulfide In N,N-dimethyl-formamide at 20℃;	94%

1-bromo-6-fluorotetradec-7-yne + (adamant-1-yl)-acetic acid (4942-47-6) → 6-fluorotetradec-7-yn-1-yl 2-((1s,3s)-adamantan-1-yl)acetate

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 75℃; for 12h; Inert atmosphere;	94%

4-((4-aminomethyl)phenoxy)phthalonitrile + (adamant-1-yl)-acetic acid (4942-47-6) → 2-(adamantan-1-yl)-N-(4-(3,4-dicyanophenoxy)benzyl)acetamide

Conditions	Yield
Stage #1: (adamant-1-yl)-acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 1h; Stage #2: 4-(4-(aminomethyl)phenoxy)phthalonitrile In dichloromethane for 10h;	93.8%

ethanol (64-17-5) + (adamant-1-yl)-acetic acid (4942-47-6) → ethyl 4-(adamant-1-yl)-phenyl acetate (15782-66-8)

Conditions	Yield
With sulfuric acid for 5h; Reflux;	93%

(adamant-1-yl)-acetic acid (4942-47-6) + 3-chlorobenzhydrazide (1673-47-8) → 2-(1-adamantylmethyl)-5-(3-chlorophenyl)-1,3,4-oxadiazole (1417863-11-6)

Conditions	Yield
Stage #1: (adamant-1-yl)-acetic acid; 3-chlorobenzhydrazide With trichlorophosphate for 4h; Reflux; Stage #2: With potassium carbonate; potassium hydroxide In water pH=8; Cooling with ice;	93%

N-butylamine (109-73-9) + (adamant-1-yl)-acetic acid (4942-47-6) → 2-(adamantan-1-yl)-N-butylacetamide (122020-51-3)

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	92%
With boron trifluoride diethyl etherate; triethylamine In toluene Heating;	77%

Upstream product

• 186581-53-3 diazomethane 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 768-90-1 1-Adamantyl bromide 
• 75-35-4 1,1-Dichloroethylene 
• 281-23-2 adamantane 
• 32314-61-7 1-nitroxyadamantane 
• 3061-65-2 2-acetoxyacrylonitrile 
• 828-51-3 1-Adamantanecarboxylic acid 
• 27174-71-6 methyl 2-(adamantan-1-yl)acetate 
• 14651-42-4 1-(bromomethyl)adamantane 
• 124-38-9 carbon dioxide 
• 144499-22-9 Phosphoric acid 2-adamantan-1-yl-1-cyano-1-(pyridin-2-ylsulfanyl)-ethyl ester dimethyl ester 
• 19835-39-3 1-(1-adamantyl)propan-2-one 
• 15782-66-8 ethyl 4-(adamant-1-yl)-phenyl acetate 

Downstream Products

• 19026-75-6 α-adamantyl acetanilide 
• 19026-77-8 1-((adamantan-1-yl)methyl)-3-phenylurea 
• 19026-73-4 2-(1-adamantyl)acetamide 
• 19026-80-3 2-[4-(tricyclo[3.3.1.1^3,7]dec-1-yl)phenyl]acetohydrazide 
• 16611-09-9 2-oxo-1-tricyclo[3.3.1.1^3,7]decanacetic acid 
• 17768-36-4 2-(3-hydroxyadamantan-1-yl)acetic acid 
• 81918-15-2 4-oxoadamantane-1-acetic acid 
• 96847-85-7 (S)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-isobutyl ester 
• 87113-91-5 (S)-1-(2-adamantan-1-yl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 911056-26-3 5-adamantan-1-ylmethyl-3-p-tolyl-[1,2,4]oxadiazole 
• 1092408-16-6 C₂₁H₂₆O₄ 
• 1348198-25-3 TPI-1343-239 
• 1061377-83-0 2-adamantan-1-yl-N-[4-fluoro-3-(3-morpholin-4-yl-propoxy)-phenyl]-acetamide 
• 1061378-19-5 2-adamantan-1-yl-N-(3-hydroxycyclohexyl)acetamide 

Relevant articles and documents

Method for preparing carboxylic acid by one-pot method

The invention discloses a method for preparing carboxylic acid by a one-pot method, which comprises the steps of carrying out a Corey-Fuchs process on 1,1-dibromo olefin under the action of n-butyllithium, reacting with isopropanol pinacol borate, quenching with hydrogen chloride, oxidizing with an oxidant, separating and purifying to obtain carboxylic acid. The method disclosed by the invention is a one-pot preparation method, is simple and convenient to operate, does not need to use metal catalysis, uses cheap and easily available reagents for reaction, is green and environment-friendly, hasmild reaction conditions and wide substrate applicability, and provides a new way for rapidly preparing a series of carboxylic acids containing different functional groups.

Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives

The Willgerodt–Kindler reaction of 1-(1-adamantyl)propan-2-one and its derivatives was studied by gas chromatography–mass spectrometry. The reaction time was found to be 3–4 times longer than in the case of alkyl aryl ketones due to considerable steric hindrances in the molecules of adamantyl ketones. The use of diglyme as solvent and sodium butyl xanthate as catalyst significantly shortened the reaction time and improved the yield to 92%.

2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids

The synthesis is reported of 2-hydroxy-1,2,2-triphenylethanone esters of carboxylic acids by the reaction between 2-chloro-1,2,2-triphenylethanone and a carboxylic acid in the presence of silver carbonate and silver tetrafluoroborate. Photolysis of the esters occurs rapidly on irradiation with a medium-pressure mercury lamp through quartz or Pyrex to return the carboxylic acid. The side product of the photolysis is benzo[b]phenanthro[9,10-d]furan, formed through a tandem process involving initial generation of 2,3-diphenylbenzofuran, photochemical cyclisation and re-aromatisation by aerial oxidation.