529-17-9

Basic information

• Product Name: 8-METHYL-8-AZABICYCLO[3.2.1]OCTANE
• Synonyms: 8-METHYL-8-AZABICYCLO[3.2.1]OCTANE;(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]octane;(1β,5β)-8-Methyl-8-azabicyclo[3.2.1]octane;1αH,5αH-Tropane;1alphaH,5alphaH-Tropane;2,3-Dihydro-8-methylnortropidine;8-Azabicyclo[3.2.1]octane, 8-methyl-;N-Methyl-8-azabicyclo[3.2.1]octane
• CAS NO: 529-17-9
• Molecular Formula: C₈H₁₅N
• Molecular Weight: 125.21
• Product Categories: Heterocyclic Compounds
• Mol File: 529-17-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 167-169 °C(lit.)
• Flash Point: 108 °F
• Appearance: /
• Density: 0.931 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.82mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• PKA: 11.57±0.20(Predicted)
• Merck: 13,9847
• CAS DataBase Reference: 8-METHYL-8-AZABICYCLO[3.2.1]OCTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-METHYL-8-AZABICYCLO[3.2.1]OCTANE(529-17-9)
• EPA Substance Registry System: 8-METHYL-8-AZABICYCLO[3.2.1]OCTANE(529-17-9)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 529-17-9(Hazardous Substances Data)

Usage

General Description

Tropane (8-methyl-8-azabicyclo[3.2.1]-octane) is a bridged bicyclic N-containing compound. The 8-methyl-8-azabicyclo[3.2.1]-octane has a tropane ring system, which is an important substructure in a number of natural products and synthetic compounds of biological and medicinal importance. Production of tropane alkaloid in callus and root cultures of seven Hyoscyamus species has been studied. Tropane derivatives are reported to undergo rapid N-methyl inversion.

InChI:InChI=1/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+

Synthetic route

tropinone (532-24-1) → tropane (529-17-9)

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide under 1.5 Torr; for 35h;	100%
With potassium hydroxide; hydrazine In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol for 8h; Wolff-Kischener reduction; Heating;

carbon monoxide (201230-82-2) + tropidine (529-18-0) → tropane (529-17-9) + tropan-2-yl-methanol (68969-37-9) + 3-hydroxymethyl-8-methyl-8-azabicyclo[3.2.1]octane (90949-82-9, 888716-28-7) + Tropan-3β-carboxaldehyd (93047-52-0, 99658-61-4)

Conditions	Yield
With hydrogen; di-μ-chlorobis(norbornadiene)dirhodium(I); tributylphosphine In benzene at 100℃; under 60004.8 Torr; for 6h;	A 2% B n/a C n/a D 92%

carbon monoxide (201230-82-2) + tropidine (529-18-0) → tropane (529-17-9) + tropan-2-yl-methanol (68969-37-9) + 3-hydroxymethyl-8-methyl-8-azabicyclo[3.2.1]octane (90949-82-9, 888716-28-7) + Tropan-3β-carboxaldehyd (93047-52-0, 99658-61-4) + 8-Methyl-8-aza-bicyclo[3.2.1]octane-2-carbaldehyde

Conditions	Yield
With hydrogen; carbonylhydridetris(triphenylphosphine)rhodium(I) In benzene at 100℃; under 60004.8 Torr; for 6h; Product distribution; various catalysts, formed in situ from various phosphines;	A 2% B n/a C n/a D 86% E 10%

N-<(benzoyloxy)carbonyl>nortropane (95799-01-2) → tropane (529-17-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Ambient temperature;	72%

1-<(methyl(4-cycloheptenyl)carbamoyl)oxy>-2(1H)-pyridinethione (122709-62-0) → tropane (529-17-9) + 2-(2-pyridylthio)tropane (128729-93-1)

Conditions	Yield
With 2-methylpropan-2-thiol; acetic acid In acetonitrile at 25℃; Irradiation;	A 68% B 3 % Chromat.

carbon monoxide (201230-82-2) + tropidine (529-18-0) → tropane (529-17-9) + Tropan-3β-carboxaldehyd (93047-52-0, 99658-61-4) + 8-Methyl-8-aza-bicyclo[3.2.1]octane-2-carbaldehyde

Conditions	Yield
With hydrogen; di-μ-chlorobis(norbornadiene)dirhodium(I); tricyclohexylphosphine In benzene at 100℃; under 60004.8 Torr; for 6h;	A 22% B 67% C 11%

1-<(methyl(4-cycloheptenyl)carbamoyl)oxy>-2(1H)-pyridinethione (122709-62-0) → tropane (529-17-9)

Conditions	Yield
With 2-methylpropan-2-thiol; acetic acid In benzene at 4℃;	67%

N-methyl-N-cycloheptylamine (42870-65-5) → tropane (529-17-9)

Conditions	Yield
With chlorine Erwaermen des erhaltenen Chlor-cycloheptyl-methyl-amins mit 84%ig. wss. Schwefelsaeure;

Tropidin (529-18-0, 122709-67-5) → tropane (529-17-9)

Conditions	Yield
With diethyl ether; platinum Hydrogenation;

3-tropanol (120-29-6) → tropane (529-17-9)

Conditions	Yield
With phosphonium iodide; hydrogen iodide at 195 - 200℃; im Rohr;

(1S,4R)-4-Methylamino-cycloheptanol → tropane (529-17-9)

Conditions	Yield
With thionyl chloride 1.) CDCl3, 0 deg C to room temperature, 19.5 h, 2.) 12 h; Yield given. Multistep reaction;

hydroscopolin → tropane (529-17-9)

Conditions	Yield
With phosphonium iodide; hydrogen iodide at 195 - 205℃; im Rohr;

tropane-6,7-diol (103392-59-2) + hydrogen iodide (10034-85-2) + phosphonium iodide → tropane (529-17-9)

Conditions	Yield
at 195 - 205℃;

hydrogen iodide (10034-85-2) + 3-tropanol (120-29-6) + phosphonium iodide → tropane (529-17-9)

Conditions	Yield
at 195 - 200℃;

diethyl ether (60-29-7) + tropidine (529-18-0) + platinum black → tropane (529-17-9)

Conditions	Yield
Hydrogenation;

tropane chloromethylate → tropane (529-17-9)

Conditions	Yield
Bei der trocknen Destillation;

hydriodide of 3-iodo-tropane → tropane (529-17-9) + Tropidin (529-18-0, 122709-67-5)

Conditions	Yield
With hydrogenchloride; zinc
With hydrogen iodide; zinc

hydrobromide of α-tropidine hydrobromide → tropane (529-17-9) + Tropidin (529-18-0, 122709-67-5)

Conditions	Yield
With sulfuric acid; zinc
With hydrogen iodide; zinc

3-iodo-tropane + hydrogenchloride (7647-01-0) + zinc dust → tropane (529-17-9) + Tropidin (529-18-0, 122709-67-5)

sulfuric acid (7664-93-9) + tropinone (532-24-1) → tropane (529-17-9) + 3-tropanol (120-29-6) + pseudotropine (135-97-7)

Conditions	Yield
elektrolytische Reduktion an einer Bleikathode;

tropinone (532-24-1) + hydrogen iodide (10034-85-2) + zinc → tropane (529-17-9) + 3-tropanol (120-29-6) + pseudotropine (135-97-7)

tropinone (532-24-1) → tropane (529-17-9) + tropine, pseudotropine

Conditions	Yield
elektrolytische Reduktion;
With hydrogen iodide; zinc

3exo-bromo-tropane (2292-11-7) + sulfuric acid (7664-93-9) + zinc → tropane (529-17-9) + Tropidin (529-18-0, 122709-67-5)

tropane iodomethylate → tropane (529-17-9) + cyclohept-3-enyl-dimethyl-amine (855405-70-8)

Conditions	Yield
With silver(l) oxide durch Destillation der entstandenen stark alkal. Loesung der Ammoniumbase;

cis-4-[(benzyloxycarbonyl)amino]cyclohept-2-enol (113340-14-0, 146309-07-1) → tropane (529-17-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 66 percent / LiAlH4 / tetrahydrofuran / 10 h / Heating 2: 90 percent / H2 / 5percent Pd on charcoal / methanol / 16 h 3: 1.) SOCl2, 2.) TABD / 1.) CDCl3, 0 deg C to room temperature, 19.5 h, 2.) 12 h View Scheme

6-Oxa-7-aza-bicyclo[3.2.2]non-8-ene-7-carboxylic acid benzyl ester (146309-04-8) → tropane (529-17-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 67 percent / LiAlH4 / tetrahydrofuran / 10 h / Heating 2: 87 percent / Zn / acetic acid / 4 h / 50 - 60 °C 3: 90 percent / H2 / 5percent Pd on charcoal / methanol / 16 h 4: 1.) SOCl2, 2.) TABD / 1.) CDCl3, 0 deg C to room temperature, 19.5 h, 2.) 12 h View Scheme

(1S,4R)-4-Methylamino-cyclohept-2-enol → tropane (529-17-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / H2 / 5percent Pd on charcoal / methanol / 16 h 2: 1.) SOCl2, 2.) TABD / 1.) CDCl3, 0 deg C to room temperature, 19.5 h, 2.) 12 h View Scheme

N-methyl-8-oxa-9-azabicyclo[3.2.2]non-6-ene (214326-04-2) → tropane (529-17-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / Zn / acetic acid / 4 h / 50 - 60 °C 2: 90 percent / H2 / 5percent Pd on charcoal / methanol / 16 h 3: 1.) SOCl2, 2.) TABD / 1.) CDCl3, 0 deg C to room temperature, 19.5 h, 2.) 12 h View Scheme

1-chloro-1-nitrosocyclohexane (695-64-7) → tropane (529-17-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: 68 percent / ethanol; CCl4 / 48 h / -10 °C 2: 98 percent / H2 / 5percent Pd/C / methanol / 7 h / 760 Torr 3: 80 percent / Na2CO3 / CHCl3; H2O / 1.) 0 deg C, 30 min, 2.) RT, 2h 4: 12 percent / SOCl2 / CHCl3 / 48 h / Ambient temperature 5: 78 percent / potassium tert-butoxide / benzene; hexamethylphosphoric acid triamide / 2 h / Ambient temperature 6: 72 percent / LiALH4 / tetrahydrofuran / 24 h / Ambient temperature View Scheme
Multi-step reaction with 6 steps 1: 68 percent / ethanol; CCl4 / 48 h / -10 °C 2: 98 percent / H2 / 5percent Pd/C / methanol / 7 h / 760 Torr 3: 80 percent / Na2CO3 / CHCl3; H2O / 1.) 0 deg C, 30 min, 2.) RT, 2h 4: SOCl2, pyridine / diethyl ether / 14 h / Ambient temperature 5: 78 percent / potassium tert-butoxide / benzene; hexamethylphosphoric acid triamide / 2 h / Ambient temperature 6: 72 percent / LiALH4 / tetrahydrofuran / 24 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: 68 percent / ethanol; CCl4 / 48 h / -10 °C 2: 98 percent / H2 / 5percent Pd/C / methanol / 7 h / 760 Torr 3: 80 percent / Na2CO3 / CHCl3; H2O / 1.) 0 deg C, 30 min, 2.) RT, 2h 5: 72 percent / LiALH4 / tetrahydrofuran / 24 h / Ambient temperature View Scheme

tropane (529-17-9) + chloroformic acid ethyl ester (541-41-3) → N-(ethoxycarbonyl)nortropane (6760-98-1)

Conditions	Yield
In benzene	95%

tropane (529-17-9) + norborn-2-ene (498-66-8) → C15H25N

Conditions	Yield
With scandium tris(ortho-N,N-dimethylaminobenzyl); trityl tetrakis(pentafluorophenyl)borate In toluene at 70℃; for 24h; regiospecific reaction;	90%

tropane (529-17-9) → 8-azabicyclo[3.2.1]octane (280-05-7)

Conditions	Yield
With carbonochloridic acid 1-chloro-ethyl ester In DCE at 0℃; for 4.08333h; Heating / reflux;	83%
With hypochloric acid Reduktion des entstandenen N-Chlor-nortropans;

tropane (529-17-9) + 2-(nonafluoro-tert-butoxy)ethyl acrylate → 6-((1R,5S)-8-azabicyclo[3.2.1]octan-8-yl)-1-((1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl)oxy)hexan-3-one

Conditions	Yield
With benzophenone; copper diacetate In acetonitrile at 35℃; for 3h; Giese Free Radical Synthesis; Darkness; Inert atmosphere; Irradiation; Sealed tube;	83%

tropane (529-17-9) + methyl vinyl ketone (78-94-4) → 5-((1R,5S)-8-azabicyclo[3.2.1]octan-8-yl)pentan-2-one

Conditions	Yield
With benzophenone; copper diacetate In acetonitrile at 35℃; for 16h; Giese Free Radical Synthesis; Darkness; Inert atmosphere; Irradiation; Sealed tube;	73%

tropane (529-17-9) → 8-azabicyclo[3.2.1]octane hydrochloride (6760-99-2)

Conditions	Yield
Stage #1: tropane With chloroformic acid ethyl ester In toluene at 80℃; for 24h; Stage #2: With hydrogenchloride In water at 100℃; for 2h;	72%
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 2: MeOH View Scheme
Multi-step reaction with 2 steps 1: 95 percent / benzene 2: 90 percent / aq. HCl / Heating View Scheme

tropane (529-17-9) + acetic anhydride (108-24-7) → 8-acetyl-nortropane (769-04-0)

Conditions	Yield
palladium diacetate at 80℃; for 14h; Neat (no solvent);	70%

tropane (529-17-9) + acrylonitrile (107-13-1) → 4-(8-azabicyclo[3.2.1]octan-8-yl)butanenitrile

Conditions	Yield
With benzophenone; copper diacetate In acetonitrile at 35℃; for 5h; Giese Free Radical Synthesis; Darkness; Inert atmosphere; Irradiation; Sealed tube;	69%

tropane (529-17-9) + phenylmagnesium bromide (100-58-3) → 8-benzyl-8-azabicyclo[3.2.1]octane (19079-79-9)

Conditions	Yield
Stage #1: tropane With 1,4-diaza-bicyclo[2.2.2]octane; tri(4-tolyl)aminium hexafluorophosphate In acetonitrile at -5℃; Inert atmosphere; Stage #2: phenylmagnesium bromide In tetrahydrofuran; acetonitrile at 0℃; for 0.0833333h; Inert atmosphere; regioselective reaction;	66%

tropane (529-17-9) + ethyl acrylate (140-88-5) → ethyl 4-(8-azabicyclo[3.2.1]octan-8-yl)butanoate

Conditions	Yield
With benzophenone; copper diacetate In acetonitrile at 35℃; for 3h; Giese Free Radical Synthesis; Darkness; Inert atmosphere; Irradiation; Sealed tube;	61%

tropane (529-17-9) + phenyl chloroformate (1885-14-9) → 8-Aza-bicyclo[3.2.1]octane-8-carboxylic acid phenyl ester

Conditions	Yield
In dichloromethane Ambient temperature;	60%

tropane (529-17-9) + benzophenone (119-61-9) → tetraphenylethane-1,2-diol (464-72-2) + 1,2-bis(8-azabicyclo<3,2,1>oct-8-yl)ethane + 2-(8-Aza-bicyclo[3.2.1]oct-8-yl)-1,1-diphenyl-ethanol

Conditions	Yield
In benzene at 22 - 25℃; for 11h; Irradiation;	A n/a B 15% C 56%

tropane (529-17-9) → tetraphenylethane-1,2-diol (464-72-2) + 1,2-bis(8-azabicyclo<3,2,1>oct-8-yl)ethane + 2-(8-Aza-bicyclo[3.2.1]oct-8-yl)-1,1-diphenyl-ethanol

Conditions	Yield
With benzophenone In benzene at 22 - 25℃; for 11h; Irradiation;	A n/a B 15% C 56%

tropane (529-17-9) → 8-formyl-nortropane (56771-95-0)

Conditions	Yield
With ruthenium tetroxide In tetrachloromethane for 2h;	49%

tropane (529-17-9) + bromocyane (506-68-3) → nortropane-8-carbonitrile

Conditions	Yield
With diethyl ether

tropane (529-17-9) + 3-(N,N,N-trimethylammonio)propyl bromide (131732-22-4) → 8ξ-methyl-8ξ-(3-trimethylammonio-propyl)-nortropanium; dibromide (109286-69-3)

Conditions	Yield
With acetonitrile

tropane (529-17-9) + benzoic acid (65-85-0) → 8-benzoyl-8-azabicyclo<3.2.1>octane (95687-85-7)

Conditions	Yield
at 190℃;

tropane (529-17-9) + 3-Phenylpropionic acid (501-52-0) → 8-(3-phenyl-propionyl)-nortropane

Conditions	Yield
at 190℃;

tropane (529-17-9) + methyl iodide (74-88-4) → 8,8-dimethyl-nortropanium; iodide (18600-24-3)

Conditions	Yield
With methanol

tropane (529-17-9) → tropane-8-oxide

Conditions	Yield
With dihydrogen peroxide

Upstream product

• 42870-65-5 N-methyl-N-cycloheptylamine 
• 529-18-0 Tropidin 
• 120-29-6 3-tropanol 
• 103392-59-2 tropane-6,7-diol 
• 10034-85-2 hydrogen iodide 
• 60-29-7 diethyl ether 
• 529-18-0 tropidine 
• 7647-01-0 hydrogenchloride 
• 532-24-1 tropinone 
• 2292-11-7 3exo-bromo-tropane 
• 7664-93-9 sulfuric acid 
• 146490-66-6 cis-4-aminocycloheptanol hydrochloride 
• 95798-89-3 8-oxa-9-azabicyclo<3.2.2>non-6-ene hydrochloride 
• 23206-17-9 5-(N-methoxycarbonylamino)cycloheptene 

Downstream Products

• 95687-85-7 8-benzoyl-8-azabicyclo<3.2.1>octane 
• 280-05-7 8-azabicyclo[3.2.1]octane 
• 56771-95-0 N-Formylnortropan 
• 464-72-2 tetraphenylethane-1,2-diol 
• 19079-79-9 8-benzyl-8-azabicyclo[3.2.1]octane 
• 769-04-0 N-Acetyl-nortropan 
• 16641-72-8 8-(phenyloxycarbonyl)-8-azabicyclo<3.2.1>octan-3-one 

Relevant articles and documents

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