4242-18-6

Basic information

• Product Name: 5,6,7,8-Tetrahydronaphthalene-1-carboxylic acid
• Synonyms: 5,6,7,8-TETRAHYDRO-1-NAPHTHALENECARBOXYLIC ACID;5,6,7,8-TETRAHYDRO-1-NAPHTHOIC ACID;5,6,7,8-TETRAHYDRO-NAPHTHALENE-1-CARBONYL ACID;5,6,7,8-TETRAHYDRONAPHTHALENE-1-CARBOXYLIC ACID;5.6.7.8-TETRAHYDRO-1-NAPHTOIC ACID;5,6,7,8-Tetrahydro-1-Naphthylenecarboxylic Acid;NSC44874;5,6,7,8-tetrahedro-1-naphthoic acid
• CAS NO: 4242-18-6
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• Product Categories: Naphthalene derivatives;INTERMEDIATESOFPALONOSETRONHYDROCHLORIDE;Organic acids;API intermediates;Intermediate of palonosetron hcl;Aromatics;Intermediates
• Mol File: 4242-18-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 150.0 to 154.0 °C
• Boiling Point: 336.8 °C at 760 mmHg
• Flash Point: 154.2 °C
• Appearance: White crystalline powder
• Density: 1.184 g/cm³
• Vapor Pressure: 4.3E-05mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.26±0.20(Predicted)
• CAS DataBase Reference: 5,6,7,8-Tetrahydronaphthalene-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-Tetrahydronaphthalene-1-carboxylic acid(4242-18-6)
• EPA Substance Registry System: 5,6,7,8-Tetrahydronaphthalene-1-carboxylic acid(4242-18-6)

Safety Data

• Hazardous Substances Data: 4242-18-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 4242-18-6 differently. You can refer to the following data:
1. 5,6,7,8-Tetrahydronaphthalene-1-carboxylic acid is an intermediate used for the preparation of the therapeutically useful antiemetic agent Palonosetron (P165805).
2. An intermediate used for the preparation of the therapeutically useful antiemetic agent Palonosetron (P165805). hydrochloride.

InChI:InChI=1/C11H12O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h3,5,7H,1-2,4,6H2,(H,12,13)

Synthetic route

8-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid (74145-11-2) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In acetic acid for 6h;	75%
With hydrogen; palladium on activated charcoal In acetic acid

1-naphthalenecarboxylic acid (86-55-5) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With hydrogen; acetic acid; palladium 10% on activated carbon at 80 - 85℃; under 2942.29 - 3677.86 Torr;	74.3%
PtO2 In acetic acid	67%
With hydrogen; acetic acid; palladium on activated charcoal at 85℃; under 2585.7 Torr;	60%

8-(2-Oxazolinyl)tetralin (75934-22-4) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With hydrogenchloride In water for 18h; Heating;	72%

1-naphthalenecarboxylic acid (86-55-5) → tetralin-1-carboxylic acid (1914-65-4) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With nickel; sodium carbonate at 75℃; under 128714 Torr; Hydrogenation;
With ethanol; nickel at 75℃; under 128714 Torr; Hydrogenation;

5,6,7,8-tetrahydro-naphthalene-1-carbaldehyde (41828-13-1) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With permanganate(VII) ion
(oxidation);

5,6,7,8-tetrahydronaphthalene-1-carbonitrile (29809-13-0) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With hydrogenchloride at 120℃; im Rohr;

5,6,7,8-tetrahydronaphthalene-1-carbonitrile (29809-13-0) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + 5,6,7,8-tetrahydro-[1]naphthamide (13052-97-6)

Conditions	Yield
With potassium hydroxide at 160 - 170℃; Trennung durch Behandeln mit Sodaloesung;

5-bromotetralin (6134-55-0) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With diethyl ether; lithium Behandeln des Reaktionsgemisches mit festem CO2;

1-naphthoic anhydride (64985-86-0) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With hydrogen; palladium In acetic acid

2,3,4-Trichlor-naphthoesaeure (91064-96-9) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With sodium hydroxide; nickel

hydrogenchloride (7647-01-0) + 5,6,7,8-tetrahydronaphthalene-1-carbonitrile (29809-13-0) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
at 120℃; im Rohr;

5.6.7.8-tetrahydro-naphthoic acid-(1)-ethyl ester → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With potassium hydroxide

5.6.7.8-tetrahydro-naphthonitrile-(1) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With sodium hydroxide at 140 - 145℃;
With hydrogenchloride at 140℃;

diazotized 6-amino-tetralin-carboxylic acid-(5) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
With ethanol; copper

5,6,7,8-tetrahydro-naphthalene-1-carbaldehyde (41828-13-1) + permanganate → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

1-naphthalenecarboxylic acid (86-55-5) + acetic acid (64-19-7) + platinum → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Hydrogenation;

1-methyl-4-nitrosobenzene (623-11-0) + 1-naphthalenecarboxylic acid (86-55-5) + nickel-aluminium-alloy → tetralin-1-carboxylic acid (1914-65-4) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

1-naphthalenecarboxylic acid (86-55-5) + acetic acid (64-19-7) + platinum oxide → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + tetrahydronaphthoic acid

Conditions	Yield
Hydrogenation;

1,2,3,4-Tetrahydro-1-naphthol (529-33-9) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) nBuLi, TMEDA / 1) pentane, reflux, 2) pentane 2: hydrogen / Pd/C / acetic acid View Scheme

1-(but-3-en-1-yl)-2-methoxybenzene (63667-83-4) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions

Yield

Multi-step reaction with 7 steps 1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / 1) in dry ether at reflux for 1h 2) CO2 as a continous stream for 1h 2: thionyl chloride 3: sodium hydroxide; boron trifluoride-tetrahydrofuran complex; dihydrogen peroxide / 1) for 1h 2) at 50 deg C for 1h 4: triethylamine / dichloromethane / -22 °C 5: lithium bromide / N,N-dimethyl-formamide 6: magnesium / tetrahydrofuran 7: hydrogenchloride / water / 18 h / Heating View Scheme

(4-iodobutyl)anisole (75934-24-6) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions

Yield

Multi-step reaction with 8 steps 1: potassium tert-butylate / tert-butyl alcohol / 24 h / 90 °C 2: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / 1) in dry ether at reflux for 1h 2) CO2 as a continous stream for 1h 3: thionyl chloride 4: sodium hydroxide; boron trifluoride-tetrahydrofuran complex; dihydrogen peroxide / 1) for 1h 2) at 50 deg C for 1h 5: triethylamine / dichloromethane / -22 °C 6: lithium bromide / N,N-dimethyl-formamide 7: magnesium / tetrahydrofuran 8: hydrogenchloride / water / 18 h / Heating View Scheme

3-(3-Butenyl)anisic Acid (75934-25-7) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: thionyl chloride 2: sodium hydroxide; boron trifluoride-tetrahydrofuran complex; dihydrogen peroxide / 1) for 1h 2) at 50 deg C for 1h 3: triethylamine / dichloromethane / -22 °C 4: lithium bromide / N,N-dimethyl-formamide 5: magnesium / tetrahydrofuran 6: hydrogenchloride / water / 18 h / Heating View Scheme

2-<2-Methoxy-3-(butenyl)phenyl>-4,4-dimethyl-2-oxazoline (75934-04-2) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide; boron trifluoride-tetrahydrofuran complex; dihydrogen peroxide / 1) for 1h 2) at 50 deg C for 1h 2: triethylamine / dichloromethane / -22 °C 3: lithium bromide / N,N-dimethyl-formamide 4: magnesium / tetrahydrofuran 5: hydrogenchloride / water / 18 h / Heating View Scheme

2-[3-(4-Bromo-butyl)-2-methoxy-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole (75934-19-9) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran 2: hydrogenchloride / water / 18 h / Heating View Scheme

4-[3-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-2-methoxy-phenyl]-butan-1-ol (75934-17-7) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / -22 °C 2: lithium bromide / N,N-dimethyl-formamide 3: magnesium / tetrahydrofuran 4: hydrogenchloride / water / 18 h / Heating View Scheme

2-[3-(4-Methanesulfonyl-butyl)-2-methoxy-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole (75948-76-4) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / LiBr / dimethylformamide 2: 84 percent / Mg / tetrahydrofuran 3: 72 percent / 4.5M HCl / H2O / 18 h / Heating View Scheme

methoxybenzene (100-66-3) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions

Yield

Multi-step reaction with 9 steps 1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / 1) in dry ether at reflux for 1h 2) -22 deg C overnight 2: potassium tert-butylate / tert-butyl alcohol / 24 h / 90 °C 3: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / 1) in dry ether at reflux for 1h 2) CO2 as a continous stream for 1h 4: thionyl chloride 5: sodium hydroxide; boron trifluoride-tetrahydrofuran complex; dihydrogen peroxide / 1) for 1h 2) at 50 deg C for 1h 6: triethylamine / dichloromethane / -22 °C 7: lithium bromide / N,N-dimethyl-formamide 8: magnesium / tetrahydrofuran 9: hydrogenchloride / water / 18 h / Heating View Scheme

(5,6,7,8-tetrahydronaphthalene-1-yl)methanol (41790-30-1) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: diluted Cr2O3-H2SO4 2: permanganate View Scheme
Multi-step reaction with 2 steps 1: Py*HClCrO3 2: (oxidation) View Scheme

2,3,4-Trichlor-naphthoesaeure-1-chlorid (94627-88-0) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / methanol / Heating 2: Raney-Ni, aq. NaOH View Scheme

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → (5,6,7,8-tetrahydronaphthalene-1-yl)methanol (41790-30-1)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 20℃; for 16h;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24.5h;	99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24.5h;	99%

desmethyl anethole trithione (18274-81-2) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 5,6,7,8-tetrahydronaphthalene-1-carboxylate (1258508-99-4)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	97.8%
Stage #1: 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Stage #2: desmethyl anethole trithione In dichloromethane at 25℃;	96%

5-amino-1,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thiophene-5-carboxylic acid ethyl ester (1092449-30-3) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 1,3-dimethyl-5-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-5,6-dihydro-4H-cyclopenta[c]thiophene-5-carboxylic acid ethyl ester (1092447-56-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	97%

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + ethyl 2-amino-5,6-dimethylindan-2-carboxylate (141104-66-7) → 5,6-dimethyl-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (1092447-57-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	92%

methanol (67-56-1) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → methyl 1,2,3,4-tetrahydro-5-naphthalenecarboxylate (66193-59-7)

Conditions	Yield
With thionyl chloride at 0℃; Inert atmosphere; Reflux;	92%

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid-5,5,8,8-d4 (105372-60-9)

Conditions	Yield
With acetic acid-d; deuterium; palladium on activated charcoal at 55℃; under 1292.9 Torr; for 24h;	88%

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + (S)-2-amino-3,3-dimethyl-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)butanamide hydrochloride → N-((S)-3,3-dimethyl-1-(((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-1-oxobutan-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 20℃;	81.3%

(2-{[5-(trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)amine hydrochloride + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → N-(2-((5-(trifluoromethyl)pyridin-2-yl)sulfonyl)ethyl)-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Conditions	Yield
Stage #1: 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.416667h; Stage #2: (2-{[5-(trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)amine hydrochloride In dichloromethane at 20℃; for 48h;	80%

3,3,3-trifluoro-2-phenylpropene (384-64-5) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 4,4-difluoro-3-phenyl-1-(5,6,7,8-tetrahydronaphthalen-1-yl)but-3-en-1-one

Conditions	Yield
With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 48h; Molecular sieve; Inert atmosphere; Sealed tube; Irradiation;	80%

4'-methylpropiophenone (5337-93-9) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → C21H20O3

Conditions	Yield
With pyridine; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; silver carbonate; silver(I) triflimide In toluene at 120℃; for 22h; Inert atmosphere;	80%

2-amino-5-trifluoromethyl-indan-2-carboxylic acid ethyl ester (1092449-33-6) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-5-trifluoromethyl-indan-2-carboxylic acid ethyl ester (1092447-60-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	78%

4-toluenesulfonyl azide (941-55-9) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 2-[(4-methylphenyl)sulfonamido]-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 50℃; for 24h;	76%

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + anthranil (271-58-9) + 1,2-dichloro-ethane (107-06-2) → C20H20ClNO3

Conditions	Yield
With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; potassium carbonate at 100℃; for 18h;	74%

N-hydroxyphthalimide (524-38-9) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 1,3-dioxoisoindolin-2-yl 5,6,7,8-tetrahydronaphthalene-1-carboxylate

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;	72%

2-amino-5-methoxy-indan-2-carboxylic acid ethyl ester (1092449-31-4) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 5-methoxy-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (1092447-58-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	70%

ethyl 2-amino-5-cyanoindan-2-carboxylate (1092449-34-7) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 5-cyano-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (1092447-73-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	70%

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + (S)-3-aminoquinuclidine dihydrochloride → N-<(S)-1-azabicyclo<2.2.2>oct-3-yl>-5,6,7,8-tetrahydronaphthalene-1-carboxamide (135729-78-1)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 27h;	69%

2-amino-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}acetamide monohydrochloride (847494-22-8) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → N-(2-(((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-2-oxoethyl)-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Conditions

Yield

Stage #1: 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid With benzotriazol-1-ol In dichloromethane at -10℃; for 0.166667h; Stage #2: 2-amino-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}acetamide monohydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 20℃;

65.7%

formaldehyd (50-00-0) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + malonic acid dimethyl ester (108-59-8) → 2,3,6,7,8,9-hexahydro-1H-cyclopentan[a]naphthalene-1-one (19346-17-9)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate at 150℃; for 18h; Inert atmosphere; Schlenk technique; regioselective reaction;	60%

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + acetonitrile (75-05-8) → acetyl-6,7,8,8a-tetrahydrobenzo[cd]indol-2(1H)-one

Conditions	Yield
With iron(III)-acetylacetonate; copper(II) nitrate; Selectfluor at 80℃; for 8h; Schlenk technique; Inert atmosphere;	59%

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + (S)-2-amino-3-methoxy-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)propenamide hydrochloride → N-((S)-3-methoxy-1-(((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-1-oxopropan-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Conditions

Yield

Stage #1: 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid With benzotriazol-1-ol In dichloromethane at -10℃; for 0.166667h; Stage #2: (S)-2-amino-3-methoxy-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)propenamide hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 20℃;

52.9%

2-amino-5-fluoroindane-2-carboxylic acid ethyl ester (1092447-26-1) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 5-fluoro-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (1092447-61-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	40%

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) + bis(2-fluorophenyl)-λ3-iodanyl trifluoromethanesulfonate → 1,2,3,4-tetrahydro-5H-naphtho[1,2-c]chromen-5-one

Conditions	Yield
With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Schlenk technique;	39%

bis(2-fluorophenyl)iodonium trifluoromethanesulfonate (1034369-95-3) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 1,2,3,4-tetrahydro-5H-naphtho[1,2-c]chromen-5-one

Conditions	Yield
With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 24h;	39%

6-amino-3-methyl-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester (1092449-32-5) + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → 3-methyl-6-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-6,7-dihydro-5H-[2]pyrin dine-6-carboxylic acid ethyl ester (1092447-59-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	19%

2-methyl-1-phenylpiperazine hydrochloride + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → (3-methyl-4-phenylpiperazin-1-yl)(5,6,7,8-tetrahydronaphthalene-1-yl)methanone

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 20℃; for 5h;	12%

(cis)-2-amino-1,3-dimethyl-indan-2-carboxylic acid ethyl ester + 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (4242-18-6) → cis-1,3-dimethyl-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	9%

Upstream product

• 6134-55-0 5-bromotetralin 
• 119-64-2 tetralin 
• 124-38-9 carbon dioxide 
• 6134-56-1 6-bromo-1,2,3,4-tetrahydronaphthalene 
• 94627-88-0 2,3,4-Trichlor-naphthoesaeure-1-chlorid 
• 41790-30-1 (5,6,7,8-tetrahydronaphthalene-1-yl)methanol 
• 100-66-3 methoxybenzene 
• 75948-76-4 2-[3-(4-Methanesulfonyl-butyl)-2-methoxy-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole 
• 75934-17-7 4-[3-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-2-methoxy-phenyl]-butan-1-ol 
• 75934-19-9 2-[3-(4-Bromo-butyl)-2-methoxy-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole 
• 75934-04-2 2-<2-Methoxy-3-(butenyl)phenyl>-4,4-dimethyl-2-oxazoline 
• 75934-25-7 3-(3-Butenyl)anisic Acid 
• 75934-24-6 (4-iodobutyl)anisole 
• 63667-83-4 1-(but-3-en-1-yl)-2-methoxybenzene 

Downstream Products

• 1186415-50-8 C₂₁H₂₂ClNO₃ 
• 4242-17-5 ethyl 5,6,7,8-tetrahydronaphthalene-1-carboxylate 
• 66193-59-7 methyl 1,2,3,4-tetrahydro-5-naphthalenecarboxylate 
• 135729-56-5 (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one 
• 3160-17-6 2-(5,6,7,8-tetrahydronaphthalene-1-yl)acetonitrile 
• 135729-78-1 N-<(S)-1-azabicyclo<2.2.2>oct-3-yl>-5,6,7,8-tetrahydronaphthalene-1-carboxamide 
• 135755-51-0 palonosetron hydrochloride 
• 135755-51-0 RS 25233-198 
• 1417700-73-2 C₂₈H₃₀F₂N₂O₃S 
• 1417700-34-5 C₂₉H₃₁F₂N₃O₃ 

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