1072015-52-1

Basic information

• Product Name: (R)-Tetrahydrofuran-3-amine hydrochloride
• Synonyms: Josiphos SL-J001-2
• CAS NO: 1072015-52-1
• Molecular Formula: C₄H₉NO*ClH
• Molecular Weight: 123.5813
• Mol File: 1072015-52-1.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-Tetrahydrofuran-3-amine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Tetrahydrofuran-3-amine hydrochloride(1072015-52-1)
• EPA Substance Registry System: (R)-Tetrahydrofuran-3-amine hydrochloride(1072015-52-1)

Safety Data

• Hazardous Substances Data: 1072015-52-1(Hazardous Substances Data)

Usage

General Description

(R)-Tetrahydrofuran-3-amine hydrochloride is a chemical compound which is classified as an organic synthetic intermediate. The "R" in the name indicates the configuration of the chiral center, and tetrahydrofuran refers to the four-carbon ring structure of the molecule, in which one of the carbons is replaced with an oxygen atom. The "3-amine" part signifies the presence of an amine group, which is an essential functionality in organic chemistry that involves a nitrogen atom bonded to one or more alkyl groups. Lastly, the term "hydrochloride" indicates that the compound forms a salt with hydrochloric acid. This chemical is often utilized in laboratory settings for various types of chemical synthesis.

Synthetic route

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 1-(6-ethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)piperidin-4-one → (R)-1-(6-ethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-N-(tetrahydrofuran-3-yl)piperidin-4-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃;	91%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + C19H19FN4O2 → (R)-1-(8-fluoro-4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-N-(tetrahydrofuran-3-yl)piperidin-4-amine

Conditions	Yield
Stage #1: [(3R)-tetrahydrofuran-3-yl]ammonium chloride; C19H19FN4O2 With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃;	87%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 1-(6-ethyl-8-fluoro-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)piperidin-4-one → (R)-1-(6-ethyl-8-fluoro-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-N-(tetrahydrofuran-3-yl)piperidin-4-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃;	77%
Stage #1: [(3R)-tetrahydrofuran-3-yl]ammonium chloride; 1-(6-ethyl-8-fluoro-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)piperidin-4-one With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 3h;	68%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 3-(5-hydroxy-1H-indazo-1-yl)benzoic acid → 3-(5-hydroxy-1H-indazol-1-yl)-N-[(3R)-tetrahydrofuran-3-yl]benzamide

Conditions	Yield
Stage #1: [(3R)-tetrahydrofuran-3-yl]ammonium chloride; 3-(5-hydroxy-1H-indazo-1-yl)benzoic acid With triethylamine In dichloromethane at 20℃; for 20h; Inert atmosphere; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 0 - 20℃; for 1h; Inert atmosphere;	73%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 1-(6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)piperidin-4-one → (R)-1-(6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-N-(tetrahydrofuran-3-yl)piperidin-4-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃;	73%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 4,6-dichloro-N-[(2R)-2-fluoro-3-hydroxy-3-methylbutyl] pyridine-3-carboxamide → 6-chloro-N-((R)-2-fluoro-3-hydroxy-3-methylbutyl)-4-(((R)-tetrahydrofuran-3-yl)amino) nicotinamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 120℃; for 12h;	69%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 4-chloro-7,8-dimethoxyquinazoline → (R)-7,8-dimethoxy-N-(tetrahydrofuran-3-yl)quinazolin-4-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 3h;	67%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 3h;	67%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 6-amino-4-fluoronicotinonitrile → (R)-6-amino-4-((tetrahydrofuran-3-yl)amino)nicotinonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; Inert atmosphere;	66%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + Benzyl bromoacetate (5437-45-6) → (R)-benzyl 2-((tetrahydrofuran-3-yl)amino)acetate

Conditions	Yield
Stage #1: [(3R)-tetrahydrofuran-3-yl]ammonium chloride With triethylamine In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: Benzyl bromoacetate With sodium iodide In tetrahydrofuran at 0 - 20℃;	60.6%

4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (897030-99-8) + [(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) → (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine (1220812-14-5)

Conditions	Yield
With triethylamine In ethanol; water Reflux;	54%

5-methyl-2,4,6-trichloropyrimidine (1780-36-5) + [(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) → (R)-2,6-dichloro-5-methyl-N-(tetrahydrofuran-3-yl)pyrimidin-4-amine

Conditions	Yield
With triethylamine In ethanol at -40 - 20℃; for 14h;	53%
With triethylamine In ethanol at 20℃; for 14h;	53%

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + C8H5F2IO2 (1113050-16-0) → C12H13FINO3 (1113050-17-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃;

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) → (3R)-tetrahydro-3-furanamine

Conditions	Yield
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine In N,N-dimethyl-formamide at 20℃; for 0.666667h;

5-amino-4,6-dichloro-2-methylpyrimidine (39906-04-2) + [(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) → R-6-Chloro-2-methyl-N4-(tetrahydro-furan-3-yl)-pyrimidine-4,5-diamine (1231220-84-0)

Conditions	Yield
With triethylamine In isopropyl alcohol for 96h; Reflux;

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → C17H22N6O5 (1374251-05-4)

Conditions	Yield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

(S)-4-nitrophenyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamate (939425-75-9) + [(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) → C25H22ClF4N3O2 (939417-75-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + C27H18ClF4N3O4 → C25H22ClF4N3O2 (1408148-00-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + methyl 4-cyclobutyl-2-(methylsulfonyl)pyrimidine-5-carboxylate (1292289-41-8) → (R)-methyl 4-cyclobutyl-2-(tetrahydrofuran-3-ylamino)pyrimidine-5-carboxylate (1292289-43-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 16h;

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + tert-butyl (2-(6-(2-chloro-4-(6-methylpyrazin-2-yl)phenyl)-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)ethyl)carbamate (1432909-99-3) → C29H32ClN7O4 (1432910-00-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere;

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + tert-butyl 6-(2-chloro-4-(3-methylpyrazin-2-yl)phenyl)-2-(methylsulfinyl)-8-(pyridin-3-ylmethyl)pyrido[2,3-d]pyrimidin-7(8H)-one (1432910-02-5) → (R)-6-(2-chloro-4-(3-methylpyrazin-2-yl)phenyl)-8-(pyridin-3-ylmethyl)-2-((tetrahydrofuran-3-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one (1432908-69-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere;	45 mg

[(3R)-tetrahydrofuran-3-yl]ammonium chloride (1072015-52-1) + 1-(4-(4-fluorophenyl)pyrimidin-5-yl)piperidine-4-carboxylic acid → 1-(4-(4-fluorophenyl)pyrimidin-5-yl)-N-((3R)-tetrahydrofuran-3-yl)piperidine-4-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 10 - 35℃; for 4h;	0.34 g
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 10 - 35℃; for 4h;	0.34 g

Downstream Products

• 111769-26-7 (3R)-tetrahydro-3-furanamine 
• 1432908-69-4 (R)-6-(2-chloro-4-(3-methylpyrazin-2-yl)phenyl)-8-(pyridin-3-ylmethyl)-2-((tetrahydrofuran-3-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 1432910-00-3 C₂₉H₃₂ClN₇O₄ 
• 1408148-00-4 C₂₅H₂₂ClF₄N₃O₂ 
• 939417-75-1 C₂₅H₂₂ClF₄N₃O₂ 
• 1113050-17-1 C₁₂H₁₃FINO₃