42711-75-1

Basic information

• Product Name: 3-HYDROXYADAMANTANE-1-CARBOXYLIC ACID
• Synonyms: 3-HYDROXYADAMANTANCARBOXYLIC ACID;3-HYDROXYADAMANTANE-1-CARBOXYLIC ACID;3-HYDROXYADAMANTANECARBOXYLIC ACID;AKOS BC-0508;1-HYDROXYADAMANTANE-3-CARBOXYLIC ACID;TIMTEC-BB SBB010113;3-Hydroxy-1-Adamantanecarboxylic Acid;3-Hydroxy--1-Amantane Carboxylic Acid
• CAS NO: 42711-75-1
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.24
• Product Categories: Adamantane derivatives;Carboxylic Acids;Carboxylic Acids;Ring Systems
• Mol File: 42711-75-1.mol
• Article Data: 30

Chemical Properties

• Melting Point: 203 °C
• Boiling Point: 357.2 °C at 760 mmHg
• Flash Point: 184 °C
• Appearance: /
• Density: 1.419 g/cm³
• Vapor Pressure: 1.55E-06mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.60±0.40(Predicted)
• CAS DataBase Reference: 3-HYDROXYADAMANTANE-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYADAMANTANE-1-CARBOXYLIC ACID(42711-75-1)
• EPA Substance Registry System: 3-HYDROXYADAMANTANE-1-CARBOXYLIC ACID(42711-75-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-37/39-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 42711-75-1(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow solid

Uses

Different sources of media describe the Uses of 42711-75-1 differently. You can refer to the following data:
1. 3-Hydroxy-1-AdaMantane Carboxylic Acid is used in the synthesis of potent pyridyl amide/sulfonamide inhibitors of 11β-HSD-1 which could be applied to a treatment of ulcers or in hormone therapy treatments relating t o cortisol.
2. 1-Carboxy-3-adamantanol is used in the synthesis of potent pyridyl amide/sulfonamide inhibitors of 11β-HSD-1 which could be applied to a treatment of ulcers or in hormone therapy treatments relating to cortisol.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1967, 1988 DOI: 10.1080/00397918808068263

InChI:InChI=1/C11H16O3/c12-9(13)10-2-7-1-8(3-10)5-11(14,4-7)6-10/h7-8,14H,1-6H2,(H,12,13)

Synthetic route

1-Adamantanecarboxylic acid (828-51-3) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
With sulfuric acid; nitric acid at 0℃;	98%
Stage #1: 1-Adamantanecarboxylic acid With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; tert-butyl alcohol at 40℃; for 0.5h; Green chemistry; Stage #2: With potassium permanganate In water; tert-butyl alcohol at 60℃; for 8.5h; Green chemistry;	94.12%
With nitric acid at 10 - 35℃; for 3.5h; Time;	92.6%

acetylacetonatocobalt(Co(AA)2) + 1-Adamantanecarboxylic acid (828-51-3) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
With acetic acid	80%

1-adamantanemethanol (770-71-8) → 1-hydroxy-3-hydroxymethyladamantane (38584-37-1) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
Stage #1: 1-adamantanemethanol With nitric acid at 20℃; for 1h; Stage #2: With hydrazine hydrate In butan-1-ol for 3h; Reflux;	A 75% B 8%

formic acid (64-18-6) + 1,3-adamantandiol (5001-18-3) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
Stage #1: 1,3-adamantandiol With sulfuric acid at 35℃; for 0.5h; Stage #2: formic acid at 20 - 40℃; for 3h;	38%

1-Adamantanecarboxylic acid (828-51-3) → 4-oxoadamantane-1-carboxylic acid (56674-87-4) + 4-hydroxyadamantane-1-carboxylic acid (81968-77-6) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
With sodium hydroxide; phosphate buffer; oxygen; iron(II) sulfate In water at 40℃; for 3h; Product distribution; investigation of the oxy-functionalization of adamantane-1-carboxylic acid;	A 12% B 5% C 34%

3-bromoadamantane-1-carboxylic acid (21816-08-0) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
With silver nitrate In 1,4-dioxane

1-Adamantanecarboxylic acid (828-51-3) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + 3-fluoro-1-adamantane-carboxylic acid (880-50-2)

Conditions	Yield
With difluoroether

1-methoxycarbonyl-3-hydroxyadamantane (68435-07-4) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
With potassium hydroxide In methanol

3-(p-Toluolsulfonyloxy)adamantan-1-carbonsaeure → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
With 1,4-dioxane; water; triethylamine solvolysis;

1-Adamantyl bromide (768-90-1) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 20 °C 1.2: 4.5 h / 10 - 35 °C 2.1: nitric acid / 5.5 h / 10 - 35 °C View Scheme

1-Adamantanecarboxylic acid (828-51-3) → 4-oxoadamantane-1-carboxylic acid (56674-87-4) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
With tert.-butylhydroperoxide; C60H66N18*3Fe(2+)*3O4S(2-) In water at 60℃; for 24h;	A 6 %Chromat. B 26 %Chromat.

formic acid (64-18-6) + 1,3-adamantandiol (5001-18-3) → 1-Adamantanecarboxylic acid (828-51-3) + adamantane-1,3-dicarboxylic acid (39269-10-8) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
Stage #1: 1,3-adamantandiol With sulfuric acid at 35℃; for 0.5h; Stage #2: formic acid at 20 - 40℃; for 3h;

1-adamanthanol (768-95-6) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 3.25 h / 10 - 35 °C 2: nitric acid / 3.5 h / 10 - 35 °C View Scheme

3-nitroxyadamantane-1-carboxylic acid (50795-82-9) → 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Conditions	Yield
With acetic acid; urea In water at 25 - 90℃; for 5h;

1,3-dimethoxy-2-hydroxy-benzene (91-10-1) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → C19H24O5

Conditions	Yield
With methanesulfonic acid at 50℃; Friedel-Crafts Alkylation;	100%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 3-iodoadamantane-1-carboxylic acid (42711-77-3)

Conditions	Yield
With hydrogen iodide at 60℃; for 16h;	99.8%
With phosphorus pentoxide; phosphoric acid; potassium iodide at 120℃; for 3h; Inert atmosphere;	95%
With phosphoric acid; phosphorus pentoxide; potassium iodide

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 3-bromoadamantane-1-carboxylic acid (21816-08-0)

Conditions	Yield
With hydrogen bromide at 90℃; for 3.5h;	99.8%
With hydrogen bromide In water at 90℃; for 4.5h;	92%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + methyl iodide (74-88-4) → 1-methoxycarbonyl-3-hydroxyadamantane (68435-07-4)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In acetone at 20℃; for 48h;	99%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1221151-98-9) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → C45H42O12

Conditions	Yield
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction;	97%

methanol (67-56-1) + 1-Adamantanecarboxylic acid (828-51-3) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → methyl adamantane-1-carboxylate (711-01-3) + 1-methoxycarbonyl-3-hydroxyadamantane (68435-07-4)

Conditions	Yield
With sulfuric acid Reflux;	A 97% B n/a

methanol (67-56-1) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 1-methoxycarbonyl-3-hydroxyadamantane (68435-07-4)

Conditions	Yield
With sulfuric acid In 1,2-dichloro-ethane for 20h; Heating;	96%
With sulfuric acid for 12h; Inert atmosphere; Reflux;

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + 25,26,27,28-tetrahydroxy-2,8,14,20-tetrathiacalix[4]arene (182496-69-1) → p-(3-carboxy-1-adamantyl)thiacalix[4]arene

Conditions	Yield
trifluorormethanesulfonic acid In trifluoroacetic acid for 24h; Heating;	96%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + 25,26,27,28-tetrakis(hydroxy)calix[4]arene (248590-47-8) → p-(3-carboxy-1-adamantyl)calix[4]arene (765943-01-9)

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid In 1,2-dichloro-ethane at 85 - 90℃; for 12h;	96%
With trifluorormethanesulfonic acid; trifluoroacetic acid In 1,2-dichloro-ethane at 60 - 65℃; for 10h;

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 1-hydroxy-3-hydroxymethyladamantane (38584-37-1)

Conditions	Yield
	95%
Stage #1: 3-hydroxyadamantane-1-carboxylic acid With sodium tetrahydroborate In tetrahydrofuran at 0 - 31℃; for 2.5h; Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 30℃; for 14.5h; Stage #3: With water In tetrahydrofuran at 0 - 10℃; for 1h;	29.5 g

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 1-fluoro-3-(trifluoromethyl)adamantane (40556-45-4)

Conditions	Yield
With sulfur tetrafluoride; water at -178 - 40℃; for 24h; Autoclave;	95%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + butan-1-ol (71-36-3) → n-butyl 3-hydroxy-1-adamantanecarboxylate (247029-06-7)

Conditions	Yield
With sulfuric acid In toluene for 5h; Heating / reflux;	94.1%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + dimethyl sulfoxide (67-68-5) → (methylthio)methyl 3-hydroxyadamantane-1-carboxylate

Conditions	Yield
With triethylamine at 160℃; under 760.051 Torr; for 20h; Pummerer Sulfoxide Rearrangement; Schlenk technique; Inert atmosphere; Green chemistry;	94%

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 2-methacryloyloxyethyl 3-hydroxy-1-adamantanecarboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 12 - 20℃; for 22h; Temperature; Reagent/catalyst; Concentration;	93.9%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + benzene (71-43-2) → 1,4-di(3-carboxy-1-adamantyl)benzene (113392-33-9)

Conditions	Yield
With sulfuric acid at 15 - 20℃; for 4h;	93%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + benzyl bromide (100-39-0) → C25H28O3

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	91%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + benzylamine (100-46-9) → N-benzyl-3-hydroxyadamantane-1-carboxamide

Conditions	Yield
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 0 - 20℃; for 18h; Inert atmosphere;	91%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + acryloyl chloride (814-68-6) → 3-carboxy-1-adamantyl acrylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice;	90.6%

sodium boron hydride (NaBH4) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 1-hydroxy-3-hydroxymethyladamantane (38584-37-1)

Conditions	Yield
In tetrahydrofuran	90%

2-hydroxypropyl methacrylate (923-26-2) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 1-methacryloyloxypropane-2-yl 3-hydroxy-1-adamantanecarboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 12 - 20℃; for 22h; Temperature; Reagent/catalyst; Solvent; Concentration;	89.8%

1,3-Benzothiazole (95-16-9) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → (1s,3r,5R,7S)-3-(benzo[d]thiazol-2-yl)adamantan-1-ol

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃; for 8h;	89%

1,3-Benzothiazole (95-16-9) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → C17H19NOS

Conditions	Yield
With [Co(dyimethylglyoximate(1-))2(pyridine)2]PF6; tetrabutylammonium acetate In ethyl acetate at 40 - 44℃; for 30h; Irradiation; Schlenk technique; Inert atmosphere;	88%

2,3,4-tri-O-acetyl-L-rhamnopyranosyl ortho-hexynylbenzoate (1230076-22-8) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → C23H32O10

Conditions	Yield
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction;	87%

(((2-(2-iodophenyl)propan-2-yl)oxy)(trifluoromethyl)sulfane) (1584705-82-7) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → (1r,3s,5R,7S)-3-((trifluoromethyl)thio)adamantan-1-ol (1624333-35-2)

Conditions	Yield
With dipotassium peroxodisulfate; sodium dodecyl sulfate; silver nitrate In water at 50℃; for 12h; Inert atmosphere;	86%

para-xylene (106-42-3) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1) → 1,4-di(3-carboxy-1-adamantyl)-2,5-dimethylbenzene (120383-96-2)

Conditions	Yield
With sulfuric acid at 15 - 20℃; for 4h;	85%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + phenylpropyolic acid (637-44-5) → C18H20O

Conditions	Yield
With dipotassium peroxodisulfate; copper; silver nitrate In water; acetonitrile at 110℃; for 12h;	85%

3-hydroxyadamantane-1-carboxylic acid (42711-75-1) + chloromethyl methyl ether (107-30-2) → methoxymethyl-3-hydroxyadamantane-1-carboxylate

Conditions	Yield
With triethylamine at 10℃; for 1h; Temperature; Inert atmosphere;	85%

Upstream product

• 828-51-3 1-Adamantanecarboxylic acid 
• 64-18-6 formic acid 
• 5001-18-3 1,3-adamantandiol 
• 50795-82-9 3-nitroxyadamantane-1-carboxylic acid 
• 768-95-6 1-adamanthanol 
• 768-90-1 1-Adamantyl bromide 
• 68435-07-4 1-methoxycarbonyl-3-hydroxyadamantane 
• 21816-08-0 3-bromoadamantane-1-carboxylic acid 
• 770-71-8 1-adamantanemethanol 

Downstream Products

• 34859-74-0 3-chloroadamantane-1-carboxylic acid 
• 42711-77-3 3-iodoadamantane-1-carboxylic acid 
• 68435-07-4 1-methoxycarbonyl-3-hydroxyadamantane 
• 142230-18-0 3-[4-((5Z,10Z,14Z,19Z)-10,15,20-Triphenyl-porphyrin-5-yl)-phenyl]-adamantane-1-carboxylic acid 
• 142230-19-1 3-{2-Methoxy-5-[(5Z,10Z,14Z,19Z)-10,15,20-tris-(4-methoxy-phenyl)-porphyrin-5-yl]-phenyl}-adamantane-1-carboxylic acid 
• 113392-33-9 1,4-di(3-carboxy-1-adamantyl)benzene 
• 214557-78-5 benzyl (3-fluoroadamantan-1-yl)carbamate 
• 120350-85-8 3-fluoro-1-(N-adamantyl) benzamide 
• 120350-84-7 3-fluoro-1-(N-adamantyl)-p-toluenesulfonamide 
• 106094-47-7 (3-fluoroadamantan-1-yl)methanol 
• 90812-24-1 3-(1-aminoethyl)adamantan-1-ol hydrochloride 
• 38584-37-1 1-hydroxy-3-hydroxymethyladamantane 
• 1401205-99-9 1-(3-benzyloxy-1-adamantyl)ethanol 
• 1401205-97-7 3-benzyloxy-1-adamantyl methyl ketone 

Relevant articles and documents

An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization

A mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation, condensation, and decarboxylation to obtain 3-hydroxy-1-acetyladamantane (IV); and finally oxidized by potassium permanganate (KMnO4) to get the target compound (I). The overall yield was about 60%, which provides a new idea for commercial production of saxagliptin intermediate.

ADAMANTANYL-SUBSTITUTED BENZAMIDE COMPOUNDS AND THEIR USE AS P2X7 RECEPTOR ANTAGONISTS

The present invention relates to adamantanyl-substituted benzamide compounds and their use as antagonists of the P2X7 purinoreceptor. The invention further relates to methods for the treatment of disease and conditions associated with the P2X7 purinoreceptor.

Synthesis method of 3-hydroxy-1-adamantanecarboxylic acid

The invention belongs to the field of organic synthesis and particularly relates to a synthesis method of 3-hydroxy-1-adamantanecarboxylic acid. In the method, with 1-adamantanecarboxylic acid being araw material and triethyl benzyl ammonium chloride (TEBAC) being a phase transfer catalyst, the 3-hydroxy-1-adamantanecarboxylic acid is prepared under alkaline conditions through hydroxylation withKMnO4. The new preparation method not only is reduced in cost and protects environment, but also is simple in operation and convenient in post-treatment. The method is high in yield, is simple in synthesis and is suitable for industrial production.