85977-52-2

Basic information

• Product Name: (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid
• Synonyms: (1S)-1,2,3,4-Tetrahydro-1-naphthalenecarboxylic Acid;D-(-)-1,2,3,4-Tetrahydro-1-naphthoic Acid;1-Naphthalenecarboxylic acid, 1,2,3,4-tetrahydro-,(1S)-;(S)-1, 2, 3, 4-Tetrahydronaphthoic acidCAS;(1S)-1-Carboxy-1,2,3,4-tetrahydronaphthalene, (1S)-1,2,3,4-Tetrahydro-1-naphthoic acid;Palonosetron interMediater B;(S)-(-)-1,2,3,4-Tetrahydro-1-naphthoic acid(W.S);(S)-1,2,3,4-Tetrahydro-1-naphthoic Acid,99%e.e.
• CAS NO: 85977-52-2
• Molecular Formula: C11H12O2
• Molecular Weight: 176.21
• Product Categories: INTERMEDIATESOFPALONOSETRONHYDROCHLORIDE;Carboxylic Acids & Deriv.;CHIRAL CHEMICALS;Aromatics;Chiral Reagents;Intermediates
• Mol File: 85977-52-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 54-56°C
• Boiling Point: 54-56°C
• Flash Point: 156.4 °C
• Appearance: /
• Density: 1.186 g/cm³
• Vapor Pressure: 2.85E-05mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Refrigerator
• Solubility: Chloroform
• PKA: 4.28±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid(85977-52-2)
• EPA Substance Registry System: (S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid(85977-52-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36-51
• Safety Statements: 26-24/25
• Hazardous Substances Data: 85977-52-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C11H12O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10H,3,5,7H2,(H,12,13)/t10-/m0/s1

Synthetic route

(R)-[1-ethoxy-1-carbonylpropan-2-yl]-(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid ester → (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran at 20℃; for 16h; Autoclave; Green chemistry;	83%

tetralin-1-carboxylic acid (1914-65-4) → (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2)

Conditions	Yield
With quinine In ethanol at 0 - 50℃; for 0.5h;	43.6%
nach Abtrennung des Cinchonin-Salzes der (R)-1.2.3.4-Tetrahydro-naphthoesaeure-(1) (s.o.) ueber das Chinin-Salz;
Multi-step reaction with 2 steps 1: water; ethanol / 2 h / Reflux 2: hydrogenchloride / water; ethyl acetate / 0.5 h View Scheme

4-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (3123-46-4) → (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: amalgamated zinc; aqueous HCl 2: nach Abtrennung des Cinchonin-Salzes der (R)-1.2.3.4-Tetrahydro-naphthoesaeure-(1) (s.o.) ueber das Chinin-Salz View Scheme

1-naphthalenecarboxylic acid (86-55-5) → (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / toluene; N,N-dimethyl-formamide / 4 h / 10 - 40 °C / Green chemistry 1.2: 2 h / 10 - 20 °C / Green chemistry 2.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 8 h / 60 °C / 15001.5 Torr / Autoclave; Green chemistry 3.1: lithium hydroxide / tetrahydrofuran / 16 h / 20 °C / Autoclave; Green chemistry View Scheme

(R)-[1-ethoxy-1-carbonylpropan-2-yl]-1-naphthoic acid ester → (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 8 h / 60 °C / 15001.5 Torr / Autoclave; Green chemistry 2: lithium hydroxide / tetrahydrofuran / 16 h / 20 °C / Autoclave; Green chemistry View Scheme

C11H12O2*C20H24N2O2 → (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2)

Conditions	Yield
With hydrogenchloride In water; ethyl acetate for 0.5h;	110 g

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) + ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate (141104-65-6) → 2-[((S)-1,2,3,4-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (1092447-54-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	100%

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (S)-(-)-1,2,3,4-tetrahydro-1-naphthoyl chloride

Conditions	Yield
With thionyl chloride In toluene at 60 - 65℃; for 2h; Reagent/catalyst; Inert atmosphere;	100%
With thionyl chloride In toluene at 35 - 70℃; for 2.5h;

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (S)-1-hydroxymethyl-1,2,3,4-tetrahydronaphthalene (151831-52-6)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 2h;	100%
Multi-step reaction with 2 steps 1: sulfuric acid / 16 h / 60 °C 2: C33H29FeMnN2O3P; hydrogen; potassium carbonate / isopropyl alcohol / 21 h / 50 °C / 37503.8 Torr / Autoclave View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (1S)-decahydronaphthalene-1-carboxylic acid

Conditions	Yield
With platinum(IV) oxide; hydrogen In acetic acid under 3000.3 Torr;	100%

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (S)-1,2,3,4-tetrahydronaphthalene-1-carboxamide

Conditions	Yield
Stage #1: (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: With ammonia In tetrahydrofuran; ethanol at 20℃; Inert atmosphere;	90%

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) + 1-bromo-2-(triisopropylsilyl)acetylene (111409-79-1) → (S)-8-((triisopropylsilyl)ethynyl)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

Conditions	Yield
With N-tert-butoxycarbonyl-L-phenylalanine; silver(I) acetate; sodium acetate; palladium diacetate In 1,2-dichloro-ethane at 60℃; for 16h; Sealed tube; Schlenk technique;	82%
With N-tert-butoxycarbonyl-L-phenylalanine; silver(I) acetate; sodium acetate; palladium diacetate In 1,2-dichloro-ethane at 60℃; for 16h;	82.24%

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) + 3-(pyridin-2-yl)-1H-1,2,4-triazol-5-amine (83417-23-6) → (S)-(5-amino-3-(pyridin-2-yl)-1H-1,2,4-triazol-1-yl)(1,2,3,4-tetrahydronaphthalen-1-yl)methanone

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 3h; regioselective reaction;	75%

ethanol (64-17-5) + (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → C13H16O2

Conditions	Yield
With sulfuric acid at 60℃; for 16h;	52%

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) + 1,3,8-triaza-spiro[4.5]decan-2,4-dione (13625-39-3) → (S)-8-(1,2,3,4-tetrahydronaphthalene-1-carbonyl)-1,3,8-triazaspiro[4.5]decane-2,4-dione

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 15h;	23.3%

(2-hydroxyethyl)(methyl)amine (109-83-1) + (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → 2-{Methyl-[(S)-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)methyl]-amino}-ethanol (780718-92-5)

Conditions	Yield
Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → methyl (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylate

Conditions	Yield
In diethyl ether

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (S)-2-methyl-1,2,3,4,8,9,10,10a-octahydronaphth<1,8-cd>azepine (123932-21-8)

Conditions	Yield
Multi-step reaction with 2 steps 2: 1.) PCl5, 2.) AlCl3 / 1.) 1,2,4-trichlorobenzene, 120 deg C, 2.) 200 deg C, 3 h View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (S)-5-chloro-2-methyl-1,2,3,4,8,9,10,10a-octahydronaphth<1,8-cd>azepine (123932-25-2)

Conditions	Yield
Multi-step reaction with 3 steps 2: 1.) PCl5, 2.) AlCl3 / 1.) 1,2,4-trichlorobenzene, 120 deg C, 2.) 200 deg C, 3 h 3: chlorine, FeCl3*6H2O / acetonitrile / 0.25 h / 0 °C View Scheme
Multi-step reaction with 3 steps 2: 1.) PCl5, 2.) AlCl3 / 1.) 1,2,4-trichlorobenzene, 120 deg C, 2.) 200 deg C, 3 h 3: chlorine, FeCl3*6H2O / acetonitrile / 0.25 h / 0 °C View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (R)-5-chloro-2-methyl-1,2,3,4,8,9,10,10a-octahydronaphth<1,8-cd>azepine (123932-23-0)

Conditions	Yield
Multi-step reaction with 3 steps 2: 1.) PCl5, 2.) AlCl3 / 1.) 1,2,4-trichlorobenzene, 120 deg C, 2.) 200 deg C, 3 h 3: chlorine, FeCl3*6H2O / acetonitrile / 0.25 h / 0 °C View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (S)-7-chloro-2-methyl-1,2,3,4,8,9,10,10a-octahydronaphth<1,8-cd>azepine (123932-29-6)

Conditions	Yield
Multi-step reaction with 3 steps 2: 1.) PCl5, 2.) AlCl3 / 1.) 1,2,4-trichlorobenzene, 120 deg C, 2.) 200 deg C, 3 h 3: chlorine, FeCl3*6H2O / acetonitrile / 0.25 h / 0 °C View Scheme
Multi-step reaction with 3 steps 2: 1.) PCl5, 2.) AlCl3 / 1.) 1,2,4-trichlorobenzene, 120 deg C, 2.) 200 deg C, 3 h 3: chlorine, FeCl3*6H2O / acetonitrile / 0.25 h / 0 °C View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → N-(1-azabicyclo[2.2.2]oct-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ylcarboxamide

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) + methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → C21H23NO3 (1207325-89-0)

Conditions	Yield
Stage #1: (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: methyl (2S)-2-amino-3-phenylpropanoate hydrochloride With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃;

3-amino-3-(3-chlorophenyl)propionic acid methyl ester (277745-44-5) + (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → C21H22ClNO3 (1269634-46-9)

Conditions	Yield
Stage #1: (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrachloromethane at 0℃; Stage #2: 3-amino-3-(3-chlorophenyl)propionic acid methyl ester With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃;

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → (S)-(1,2,3,4-tetrahydronaphthalen-1-yl)methanamine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: borane-THF / tetrahydrofuran / 55 °C / Inert atmosphere View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → methyl 3-{[(1S)-1,2,3,4-tetrahydronaphthalen-1-ylmethyl]amino}pyridine-4-carboxylate (1616267-17-4)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: borane-THF / tetrahydrofuran / 55 °C / Inert atmosphere 3.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 1.5 h / 128 °C / Microwave irradiation; Inert atmosphere View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → 3-{[(1S)-1,2,3,4-tetrahydronaphthalen-1-ylmethyl]amino}pyridine-4-carboxylic acid (1616266-02-4)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: borane-THF / tetrahydrofuran / 55 °C / Inert atmosphere 3.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 1.5 h / 128 °C / Microwave irradiation; Inert atmosphere 4.1: sodium hydroxide / methanol / 1 h / 50 °C / Inert atmosphere View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → C19H25ClN2O

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / toluene / 2.5 h / 35 - 70 °C 2.1: toluene / 1.5 h / 70 °C / Industrial scale 3.1: boron trifluoride methanol complex; sodium tetrahydroborate / methanol / 3.3 h / -5 - 105 °C 3.2: 1 h / 70 °C / Cooling with ice 3.3: 35 °C 4.1: toluene / 12.08 h / 12 - 105 °C View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → palonosetron

Conditions

Yield

Multi-step reaction with 5 steps 1.1: thionyl chloride / toluene / 2.5 h / 35 - 70 °C 2.1: toluene / 1.5 h / 70 °C / Industrial scale 3.1: boron trifluoride methanol complex; sodium tetrahydroborate / methanol / 3.3 h / -5 - 105 °C 3.2: 1 h / 70 °C / Cooling with ice 3.3: 35 °C 4.1: toluene / 12.08 h / 12 - 105 °C 5.1: boron trifluoride methanol complex / 3.5 h / 40 - 105 °C / Industrial scale 5.2: 0.5 h / 105 °C / Industrial scale 5.3: Industrial scale View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → palonosetron hydrochloride

Conditions	Yield
Multi-step reaction with 6 steps 1.1: thionyl chloride / toluene / 2.5 h / 35 - 70 °C 2.1: toluene / 1.5 h / 70 °C / Industrial scale 3.1: boron trifluoride methanol complex; sodium tetrahydroborate / methanol / 3.3 h / -5 - 105 °C 3.2: 1 h / 70 °C / Cooling with ice 3.3: 35 °C 4.1: toluene / 12.08 h / 12 - 105 °C 5.1: boron trifluoride methanol complex / 3.5 h / 40 - 105 °C / Industrial scale 5.2: 0.5 h / 105 °C / Industrial scale 5.3: Industrial scale 6.1: hydrogenchloride / water / 0.08 h / Industrial scale View Scheme
Multi-step reaction with 4 steps 1.1: thionyl chloride / toluene / 2 h / 60 - 65 °C / Inert atmosphere 2.1: L-Selectride / tetrahydrofuran / 1 h / 5 - 15 °C / Inert atmosphere 3.1: ethanol / 4 h / 15 - 25 °C / Inert atmosphere 3.2: 2 h / 15 - 25 °C / Inert atmosphere 4.1: toluene / 14 h / 0 - 20 °C / Inert atmosphere 4.2: 5 h / 100 - 110 °C 4.3: 1 h / 100 - 110 °C View Scheme
Multi-step reaction with 4 steps 1.1: thionyl chloride / toluene / 2 h / 60 - 65 °C / Inert atmosphere 2.1: ethyl acetate / 2 h / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 - 10 °C / Reflux 4.1: toluene / 14 h / 0 - 20 °C / Inert atmosphere 4.2: 5 h / 100 - 110 °C 4.3: 1 h / 100 - 110 °C View Scheme
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / ethyl acetate / 1.05 h / 20 °C 1.2: 3 h / 50 °C 2.1: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran / 3 h / 15 - 65 °C 3.1: bis(trichloromethyl) carbonate / toluene / 3.5 h / Reflux 3.2: 4 h / Reflux 3.3: 2 h / Reflux View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalene-1S-carboxamide

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 2.5 h / 35 - 70 °C 2: toluene / 1.5 h / 70 °C / Industrial scale View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 2 h / 60 - 65 °C / Inert atmosphere 2: ethyl acetate / 2 h / 20 °C View Scheme

(S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (85977-52-2) → C18H26N2

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / toluene / 2.5 h / 35 - 70 °C 2.1: toluene / 1.5 h / 70 °C / Industrial scale 3.1: boron trifluoride methanol complex; sodium tetrahydroborate / methanol / 3.3 h / -5 - 105 °C 3.2: 1 h / 70 °C / Cooling with ice 3.3: 35 °C View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / toluene / 2 h / 60 - 65 °C / Inert atmosphere 2.1: L-Selectride / tetrahydrofuran / 1 h / 5 - 15 °C / Inert atmosphere 3.1: ethanol / 4 h / 15 - 25 °C / Inert atmosphere 3.2: 2 h / 15 - 25 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / toluene / 2 h / 60 - 65 °C / Inert atmosphere 2: ethyl acetate / 2 h / 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 - 10 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / ethyl acetate / 1.05 h / 20 °C 1.2: 3 h / 50 °C 2.1: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran / 3 h / 15 - 65 °C View Scheme

Upstream product

• 1914-65-4 tetralin-1-carboxylic acid 
• 3123-46-4 4-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 
• 86-55-5 1-naphthalenecarboxylic acid 

Downstream Products

• 177793-79-2 N-(1-azabicyclo[2.2.2]oct-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ylcarboxamide 
• 1207325-89-0 C₂₁H₂₃NO₃ 
• 1269634-46-9 C₂₁H₂₂ClNO₃ 
• 135729-60-1 palonosetron 
• 135755-51-0 palonosetron hydrochloride 
• 177793-79-2 N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalene-1S-carboxamide 
• 177793-80-5 C₁₈H₂₆N₂ 
• 18278-24-5 (S)-(-)-1,2,3,4-tetrahydro-1-naphthaldehyde 

Relevant articles and documents

Preparation method of high-purity palonosetron hydrochloride

The invention discloses a preparation method of high-purity palonosetron hydrochloride. A synthesis method is as follows: taking 1,2,3,4-tetrahedro-naphthoic acid as a starting raw material, taking quinine as a resolving agent to obtain chiral(S)-1,2,3,4-tetrahedro-naphthoic acid, acylating the chiral(S)-1,2,3,4-tetrahedro-naphthoic acid by using oxalyl chloride, and then reacting with (S)-3-aminoquinuclidine ammonia salt to obtain amide compound; concentrating, adding water to dilute, adding alkali to adjust pH value to obtain (R)-N-((S)-3-quinine)-1,2,3,4-tetralyl-1-formamide; performing reduction reaction on an intermediate under the existence of the sodium borohydride and boron trifluoride diethyl etherate so as to obtain (R)-N-(1-((S)-1,2,3,4-tetralyl)methyl)-3-quinine amine, continuously reacting with the triphosgene and boron trifluoride diethyl etherate, salting, extracting and regulating the pH value to obtain a crude product of the Palonosetron after the reaction is completed; and salting and refining the crude product in isopropanol so as to obtain the Palonosetron Hydrochloride with high purity. The preparation method not only solves the problem that the palonosetron hydrochloride is low in yield and unstable in process for a long time, but also adopts class-three solvent ethyl acetate to extract in the synthesis of each step, the invention is in favor of the environmental protection, and convenient for solvent recycling and cost saving, and is suitable for industrial production.

Method for chiral preparation of (S)-tetrahydro-1-naphthoic acid and derivative thereof

The invention relates to a method for chiral preparation of (S)-tetrahydro-1-naphthoic acid shown in a formula (V) and a derivative of (S)-tetrahydro-1-naphthoic acid. The method comprises steps as follows: (a) naphthoic acid shown in the formula (I), the derivative of naphthoic acid and (R)-2-hydroxycarboxylate shown in a formula (II) are subjected to an esterification reaction to produce naphthoate shown in a formula (III) and a derivative of naphthoate; (b) naphthoate shown in the formula (III) and the derivative of naphthoate are subjected to a hydrogenation reduction reaction in a proper solvent under the action of a metal catalyst, (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylate shown in a formula (IV) and a derivative of (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylate are obtained; (c) (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylate shown in the formula (IV) and the derivative of (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylate are hydrolyzed under the alkaline condition, and (S)-1,2,3,4-tetrahydro-1-naphthoic acid and the derivative thereof are obtained. The novel method which is different from methods in the prior art is simple to operate, green, environment-friendly, high in atom economy and suitable for industrial production and is used for chiral preparation of (S)-1,2,3,4-tetrahydro-1-naphthoic acid and the derivative thereof.