121629-14-9

Basic information

• Product Name: Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester
• Synonyms: Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester;4,4-Difluorocyclohexanecarboxylic acid methyl ester;methyl 4,4-difluorocyclohexane-1-carboxylate
• CAS NO: 121629-14-9
• Molecular Formula: C₈H₁₂F₂O₂
• Molecular Weight: 178.18
• Product Categories: Drug Intermediates
• Mol File: 121629-14-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 182℃
• Flash Point: 62℃
• Appearance: /
• Density: 1.13
• Vapor Pressure: 0.836mmHg at 25°C
• Refractive Index: 1.411
• CAS DataBase Reference: Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester(121629-14-9)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester(121629-14-9)

Safety Data

• Hazardous Substances Data: 121629-14-9(Hazardous Substances Data)

Usage

General Description

Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester is a chemical compound with the molecular formula C9H24O2F2. It is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals due to its unique chemical properties. Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester is a colorless liquid with a faint odor, and it is often used in research and development as a building block for the production of various organic compounds. It has potential applications in the pharmaceutical industry, particularly in the development of new drugs for various medical conditions. Additionally, it can be used in the synthesis of agricultural chemicals and specialty chemicals, making it a versatile and valuable compound in the field of organic chemistry.

InChI:InChI=1/C8H12F2O2/c1-12-7(11)6-2-4-8(9,10)5-3-6/h6H,2-5H2,1H3

Synthetic route

4,4-difluorocyclohexanecarboxylic acid (122665-97-8) + methanol (67-56-1) → methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9)

Conditions	Yield
With sulfuric acid at 0 - 70℃; for 16h;	90.82%
sulfuric acid for 16h; Reflux;

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) + dimethyl methane phosphonate (756-79-6) → dimethyl [2-(4,4-difluorocyclohexyl)-2-oxoethyl]phosphonate (1402838-40-7)

Conditions	Yield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: methyl 4,4-difluorocyclohexane-1-carboxylate In tetrahydrofuran at -78 - 0℃; for 1.5h; Inert atmosphere;	82%

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (4,4-difluorocyclohexyl)methanol (178312-48-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;	81%
Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With potassium hydroxide In tetrahydrofuran; diethyl ether; water at 0℃; for 1h; Inert atmosphere;	81%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18h; Inert atmosphere;	77%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	71.55%
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; ethanol at 0 - 20℃;

chloro-trimethyl-silane (75-77-4) + methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → ((4,4-difluorocyclohexylidene)(methoxy)methoxy)trimethylsilane

Conditions	Yield
Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 12h;	72%

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) + methyl iodide (74-88-4) → methyl 4,4-difluoro-1-methylcyclohexanecarboxylate (1360568-90-6)

Conditions	Yield
Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 2h; Stage #2: methyl iodide In tetrahydrofuran at 20℃;

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (2S,3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-methylphenyl)6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1360569-34-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 120 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1360569-47-6)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere 5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere 7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (2S,3R4R5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1360569-48-7)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere 5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere 7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 8.1: ammonia / methanol / 20 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (4,4-difluoro-1-methylcyclohexyl)methanol (1360568-91-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (4,4-difluoro-1-methylcyclohexyl)methyl 4-methylbenzenesulfonate (1360568-92-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → 4-bromo-1-chloro-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)benzene (1360569-03-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → 4-bromo-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-1-fluorobenzene (1360569-12-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (3R,4S,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (1360569-13-6)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere 5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1360569-14-7)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere 5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1360569-41-0)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere 7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 8.1: ammonia / methanol / 20 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)tetratydro-2H-3,4,5-triyl triacetate (1360569-42-1)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere 7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (3R,4S,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (1360569-04-5)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (3R,4R,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1360569-05-6)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (4,4-difluorocyclohexyl)methyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 2: dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (4,4-difluorocyclohexyl)methyl 2-pyridyl carbonate

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 2: dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (4,4-difluorocyclohexyl)methyl 2-oxopyridine-1-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 2: dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → 4,4-difluorocyclohexane carboxyaldehyde (265108-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 1 h / 0 °C / Inert atmosphere 2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 2 h / 0 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → [(Z)-4-(4,4-difluorocyclohexyl)but-3-enoxy]methylbenzene + [(E)-4-(4,4-difluorocyclohexyl)but-3-enoxy]methylbenzene

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -30 °C / Inert atmosphere 3.2: 16.5 h / -30 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 1 h / 0 °C / Inert atmosphere 2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -30 °C / Inert atmosphere 3.2: 16 h / -30 - 20 °C / Inert atmosphere View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → methyl (R)-4,4-difluoro-1-(1-(4-methoxyphenyl)allyl)cyclohexane-1-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2 h / -78 °C 1.2: 12 h / 20 °C 2.1: C55H54IrNO4P(1+)*BF4(1-); tetrabutylammonium benzoate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere; Sealed tube View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (4,4-difluorocyclohexyl)methyl methanesulfonate (194427-24-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 °C / Inert atmosphere 2: triethylamine / dichloromethane / 4 h / 0 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → 1-(4,4-difluorocyclohexylmethyl)-3,7-dimethyl-3,7-dihydropurine-2,6-dione

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 °C / Inert atmosphere 2: triethylamine / dichloromethane / 4 h / 0 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 3 h / 120 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (3-bromo-2-thienyl)-(4,4-difluorocyclohexyl)methanol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C 3.1: n-butyllithium; diisopropylamine / diethyl ether / 1 h / -78 °C 3.2: 1 h / -78 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → 1-[(3-bromothien-2-yl)(4,4-difluorocyclohexyl)methyl]-1H-imidazole

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C 3.1: n-butyllithium; diisopropylamine / diethyl ether / 1 h / -78 °C 3.2: 1 h / -78 °C 4.1: acetonitrile / 16 h / 80 °C View Scheme

methyl 4,4-difluorocyclohexane-1-carboxylate (121629-14-9) → (1S)-1-(4,4-difluorocyclohexyl)but-3-en-1-ol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C 3.1: indium; (1S,2R)-2-Amino-1,2-diphenylethanol; pyridine / tetrahydrofuran / 3 h / 18 °C / Inert atmosphere 3.2: 2 h / -78 °C / Inert atmosphere View Scheme

Upstream product

• 122665-97-8 4,4-difluorocyclohexanecarboxylic acid 
• 67-56-1 methanol 

Downstream Products

• 178312-48-6 (4,4-difluorocyclohexyl)methanol 
• 1360568-90-6 methyl 4,4-difluoro-1-methylcyclohexanecarboxylate 
• 1360569-34-1 (2S,3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-methylphenyl)6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1360569-47-6 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1360569-48-7 (2S,3R₄R₅S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1360568-91-7 (4,4-difluoro-1-methylcyclohexyl)methanol 
• 1360568-92-8 (4,4-difluoro-1-methylcyclohexyl)methyl 4-methylbenzenesulfonate 
• 1360569-03-4 4-bromo-1-chloro-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)benzene 
• 1360569-12-5 4-bromo-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-1-fluorobenzene 
• 1360569-13-6 (3R,4S,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1360569-14-7 (3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1402838-40-7 dimethyl [2-(4,4-difluorocyclohexyl)-2-oxoethyl]phosphonate 
• 194427-24-2 (4,4-difluorocyclohexyl)methyl methanesulfonate 
• 265108-36-9 4,4-difluorocyclohexane carboxyaldehyde 

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Provided are compounds of formula I and formula II or pharmaceutically acceptable salts of the compounds and pharmaceutical compositions thereof. The compounds of formula I and formula II or the pharmaceutically acceptable salts of the compounds provide indole 2,3-dioxygenase (IDO) inhibitory activity and are capable of treating IDO-mediated immunosuppressive diseases, such as infectious diseases or cancer.

Fluorinated carbocylic compounds

Fluoro-substituted carbocyclic compounds are prepared by (A) reacting hydrogen fluoride with a chloro-cyclohexenyl compound of the formula STR1 where R1 and R2 are independently selected from the group consisting of --H, --CH2 OH, --COF, --COCl, --CF3, --CN, STR2 and --CH2 R, where R is --H or alkyl of 1-4 carbon atoms, to form a gem-dihalocyclohexane compound of the formula STR3 where X is chlorine and R1 and R2 are as defined above, (B) dehydrohalogenating the gem-dihalocyclohexane compound in the vapor phase to form a fluoro-cyclohexenyl compound of the formula STR4 (C) contacting the fluoro-cyclohexenyl compound, in the vapor phase, with a dehydrogenation catalyst to form a fluoro-substituted aromatic compound of the formula STR5