Product Name

  • Name

    BENZOYLECGONINE

  • EINECS 208-263-5
  • CAS No. 519-09-5
  • Article Data18
  • CAS DataBase
  • Density 1.297 g/cm3
  • Solubility
  • Melting Point 195 °C
  • Formula C16H19NO4
  • Boiling Point 442.439 °C at 760 mmHg
  • Molecular Weight 289.331
  • Flash Point 221.38 °C
  • Transport Information UN 1230 3
  • Appearance Crystalline Solid
  • Safety 16-36/37-45
  • Risk Codes 11-23/24/25-39/23/24/25-25
  • Molecular Structure Molecular Structure of 519-09-5 (BENZOYLECGONINE)
  • Hazard Symbols ToxicT；FlammableF
  • Synonyms 1aH,5aH-Tropane-2b-carboxylic acid, 3b-hydroxy-, benzoate (ester) (8CI);8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 3-(benzoyloxy)-8-methyl-, [1R-(exo,exo)]-;Ecgonine, benzoate (6CI,7CI);(-)-Benzoylecgonine;Benzoylecgonine;O-Benzoyl-(-)-ecgonine;O-Benzoylecgonine;
  • PSA 66.84000
  • LogP 1.71720

Synthetic route

RTI-128
155748-84-8

RTI-128

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
With sodium nitrite In acetic anhydride; acetic acid 1.) 0 deg C, 16 h, 2.) room temperature, 8 h;93%
(-)-cocaine hydrochloride
53-21-4

(-)-cocaine hydrochloride

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
With ammonia; water86%
With dipotassium hydrogenphosphate; potassium dihydrogenphosphate In tetrahydrofuran; water at 80℃; for 3h;83%
With sodium hydroxide for 12h; Heating; Yield given;
Cocaine
50-36-2

Cocaine

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
With water for 24h; Reflux;84%
With human carboxylesterase 1b, recombinant In aq. phosphate buffer at 37℃; for 1h; pH=7.4; Enzymatic reaction;
With water In 1,4-dioxane at 130℃; for 2h; Microwave irradiation;
benzoic acid anhydride
93-97-0

benzoic acid anhydride

ecgonine
481-37-8

ecgonine

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
With acetone
With water at 100℃;
Cocaine
50-36-2

Cocaine

A

methanol
67-56-1

methanol

B

benzoic acid
65-85-0

benzoic acid

C

ecgonine
481-37-8

ecgonine

D

methyl ecgonine
7143-09-1

methyl ecgonine

E

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
With hydrogenchloride In water at 70 - 90℃; Product distribution; Rate constant; Thermodynamic data; also in plasma and with other reagents ; ΔHa, ΔS(excit.), Arrhenius parameters;
...Expand
Cocaine
50-36-2

Cocaine

A

methyl ecgonine
7143-09-1

methyl ecgonine

B

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
at 37℃; Rate constant; various pH from 6.9 to 10.4; I=0.1 M;
water
7732-18-5

water

benzoic acid anhydride
93-97-0

benzoic acid anhydride

ecgonine
481-37-8

ecgonine

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
at 100℃;
at 100℃;
...Expand
water
7732-18-5

water

Cocaine
50-36-2

Cocaine

benzylecgonine
519-09-5

benzylecgonine

l-cocaine

l-cocaine

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
With water
Cocaine
50-36-2

Cocaine

A

methylecgonine benzoate

methylecgonine benzoate

B

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
cocE-pIX Enzyme kinetics; Enzymatic reaction;
cocE-pIII Enzyme kinetics; Enzymatic reaction;
cocE Enzyme kinetics; Enzymatic reaction;
anhydroecgonine hydrochloride
74242-55-0

anhydroecgonine hydrochloride

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature
2: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h
3: toluene / 24 h / Heating
4: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
5: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
8: 80 percent / 0.67 h / 105 - 110 °C
9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Multi-step reaction with 13 steps
1: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature
2: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h
3: toluene / 24 h / Heating
4: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
5: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
8: 80 percent / 0.67 h / 105 - 110 °C
9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Multi-step reaction with 13 steps
1: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature
2: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h
3: NaIO4 / H2O / 2 h / Ambient temperature
4: 57 percent / 75 °C / 0.08 - 0.1 Torr
5: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h
6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
8: 80 percent / 0.67 h / 105 - 110 °C
9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,5S)-8-Methyl-2-phenylselanyl-8-aza-bicyclo[3.2.1]octane

(1R,5S)-8-Methyl-2-phenylselanyl-8-aza-bicyclo[3.2.1]octane

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: toluene / 24 h / Heating
2: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
3: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
6: 80 percent / 0.67 h / 105 - 110 °C
7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Multi-step reaction with 11 steps
1: toluene / 24 h / Heating
2: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
3: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
6: 80 percent / 0.67 h / 105 - 110 °C
7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Multi-step reaction with 11 steps
1: NaIO4 / H2O / 2 h / Ambient temperature
2: 57 percent / 75 °C / 0.08 - 0.1 Torr
3: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h
4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
6: 80 percent / 0.67 h / 105 - 110 °C
7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
C14H19NOSe
208038-05-5

C14H19NOSe

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 57 percent / 75 °C / 0.08 - 0.1 Torr
2: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h
3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
5: 80 percent / 0.67 h / 105 - 110 °C
6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,5R)-8-Methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid; hydrochloride

(1R,5R)-8-Methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid; hydrochloride

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h
2: toluene / 24 h / Heating
3: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
4: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
5: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
6: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
7: 80 percent / 0.67 h / 105 - 110 °C
8: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
9: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
10: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
11: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
12: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Multi-step reaction with 12 steps
1: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h
2: toluene / 24 h / Heating
3: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
4: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
5: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
6: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
7: 80 percent / 0.67 h / 105 - 110 °C
8: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
9: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
10: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
11: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
12: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Multi-step reaction with 12 steps
1: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h
2: NaIO4 / H2O / 2 h / Ambient temperature
3: 57 percent / 75 °C / 0.08 - 0.1 Torr
4: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h
5: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
6: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
7: 80 percent / 0.67 h / 105 - 110 °C
8: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
9: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
10: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
11: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
12: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
tropidine
208037-81-4

tropidine

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) 1-chloroethyl chloroformate, 3.) Et3N / 1.) toluene, reflux, 16 h, 2.) MeOH, reflux, 16 h, 3.) room temperature, 14 h
2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
4: 80 percent / 0.67 h / 105 - 110 °C
5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one
208037-76-7

(1R,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 96 percent / H2 / Pd/C / methanol / 5 h
2: 88 percent / methanol / 2 h / Ambient temperature
3: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h
4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
6: 80 percent / 0.67 h / 105 - 110 °C
7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,5S)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester
208037-78-9

(1R,5S)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
2: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
3: 80 percent / 0.67 h / 105 - 110 °C
4: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
5: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
6: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
7: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
8: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone
208037-77-8

(1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 88 percent / methanol / 2 h / Ambient temperature
2: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h
3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
5: 80 percent / 0.67 h / 105 - 110 °C
6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(2R,5S)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester
208037-73-4

(2R,5S)-5-[1'-(2'-methoxycarbonyl)ethyl]proline methyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 93 percent / Et3N / methanol / 14 h / Ambient temperature
2: 85 percent / KHMDS / tetrahydrofuran / 6 h / -78 °C
3: 87 percent / NaI / pyridine / 7.5 h
4: 88 percent / methanol / 2 h / Ambient temperature
5: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h
6: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
7: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
8: 80 percent / 0.67 h / 105 - 110 °C
9: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
10: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
11: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
12: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
13: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Multi-step reaction with 14 steps
1: 96 percent / K2CO3 / acetonitrile / 14 h / Ambient temperature
2: 90 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C
3: 90 percent / NaI / pyridine / 8 h / Heating
4: 96 percent / H2 / Pd/C / methanol / 5 h
5: 88 percent / methanol / 2 h / Ambient temperature
6: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h
7: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
8: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
9: 80 percent / 0.67 h / 105 - 110 °C
10: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
11: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
12: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
13: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
14: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(2R,5S)-5-(2-Carboxy-ethyl)-pyrrolidine-2-carboxylic acid tert-butyl ester
208037-72-3

(2R,5S)-5-(2-Carboxy-ethyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 95 percent / AcCl / 14 h / Heating
2: 93 percent / Et3N / methanol / 14 h / Ambient temperature
3: 85 percent / KHMDS / tetrahydrofuran / 6 h / -78 °C
4: 87 percent / NaI / pyridine / 7.5 h
5: 88 percent / methanol / 2 h / Ambient temperature
6: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h
7: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
8: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
9: 80 percent / 0.67 h / 105 - 110 °C
10: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
11: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
12: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
13: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
14: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Multi-step reaction with 15 steps
1: 95 percent / AcCl / 14 h / Heating
2: 96 percent / K2CO3 / acetonitrile / 14 h / Ambient temperature
3: 90 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C
4: 90 percent / NaI / pyridine / 8 h / Heating
5: 96 percent / H2 / Pd/C / methanol / 5 h
6: 88 percent / methanol / 2 h / Ambient temperature
7: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h
8: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
9: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
10: 80 percent / 0.67 h / 105 - 110 °C
11: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
12: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
13: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
14: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
15: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,2R,3S,5S)-2-cyano-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
208037-85-8

(1R,2R,3S,5S)-2-cyano-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
2: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
3: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
4: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
5: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
methyl 8-benzyl-2-hydroxy-8-azabicyclo[3.2.1]oct-2-ene-3-carboxylate
208037-75-6

methyl 8-benzyl-2-hydroxy-8-azabicyclo[3.2.1]oct-2-ene-3-carboxylate

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 90 percent / NaI / pyridine / 8 h / Heating
2: 96 percent / H2 / Pd/C / methanol / 5 h
3: 88 percent / methanol / 2 h / Ambient temperature
4: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h
5: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
6: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
7: 80 percent / 0.67 h / 105 - 110 °C
8: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
9: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
10: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
11: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
12: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
Benzoic acid (1R,2R,3S,5S)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester
208037-88-1

Benzoic acid (1R,2R,3S,5S)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
2: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,2R,3S,5S)-2-Carbamoyl-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
208037-86-9

(1R,2R,3S,5S)-2-Carbamoyl-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
2: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
3: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
4: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,2S,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
208037-82-5

(1R,2S,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
4: 80 percent / 0.67 h / 105 - 110 °C
5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,2R,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
208038-13-5

(1R,2R,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
2: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
3: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
4: 80 percent / 0.67 h / 105 - 110 °C
5: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
6: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
7: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
8: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
9: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,2S,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 1-chloro-ethyl ester
208037-92-7

(1R,2S,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 1-chloro-ethyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
2: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
5: 80 percent / 0.67 h / 105 - 110 °C
6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,2R,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 1-chloro-ethyl ester

(1R,2R,5S)-2-Phenylselanyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid 1-chloro-ethyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h
2: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature
3: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
4: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
5: 80 percent / 0.67 h / 105 - 110 °C
6: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
7: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
8: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
9: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
10: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
(1R,5S)-2-Hydroxy-8-aza-bicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester 3-methyl ester
208037-90-5

(1R,5S)-2-Hydroxy-8-aza-bicyclo[3.2.1]oct-2-ene-3,8-dicarboxylic acid 8-tert-butyl ester 3-methyl ester

benzylecgonine
519-09-5

benzylecgonine

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 87 percent / NaI / pyridine / 7.5 h
2: 88 percent / methanol / 2 h / Ambient temperature
3: 70 percent / NaH / toluene / 1.) room temperature, 30 min, 2.) reflux, 5 h
4: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h
5: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h
6: 80 percent / 0.67 h / 105 - 110 °C
7: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature
8: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature
9: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature
10: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature
11: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h
View Scheme
diazomethane
186581-53-3, 908094-01-9

diazomethane

benzylecgonine
519-09-5

benzylecgonine

Cocaine
50-36-2

Cocaine

Conditions
ConditionsYield
In dichloromethane95%
benzylecgonine
519-09-5

benzylecgonine

trimethyleneglycol
504-63-2

trimethyleneglycol

1-hydroxy-3-propyl benzoylecgonine

1-hydroxy-3-propyl benzoylecgonine

Conditions
ConditionsYield
Stage #1: benzylecgonine With 1,1'-carbonyldiimidazole In dichloromethane at 20℃;
Stage #2: trimethyleneglycol In DMF (N,N-dimethyl-formamide); dichloromethane at 20℃;		95%
Stage #1: benzylecgonine With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 24h;
Stage #2: trimethyleneglycol In dichloromethane
Stage #1: benzylecgonine With 1,1'-carbonyldiimidazole In dichloromethane for 22h;
Stage #2: trimethyleneglycol In dichloromethane at 20℃; for 6h;
propan-1-ol
71-23-8

propan-1-ol

benzylecgonine
519-09-5

benzylecgonine

RTI 13
64091-46-9

RTI 13

Conditions
ConditionsYield
With hydrogenchloride at 0℃; for 48h;83%
ethyl iodide
75-03-6

ethyl iodide

benzylecgonine
519-09-5

benzylecgonine

cocaethylene
529-38-4

cocaethylene

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In dichloromethane for 72h; Ambient temperature;72%
With ethanol at 100℃; im Rohr;
benzyl 6-bromohexanoate
78277-26-6

benzyl 6-bromohexanoate

benzylecgonine
519-09-5

benzylecgonine

(1R,2R,3S,5S)-3-Benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-benzyloxycarbonyl-pentyl ester
173443-26-0

(1R,2R,3S,5S)-3-Benzoyloxy-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 5-benzyloxycarbonyl-pentyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 80℃;72%
6-amino-hexanoic acid benzyl ester toluene-4-sulfonic acid
5514-99-8

6-amino-hexanoic acid benzyl ester toluene-4-sulfonic acid

benzylecgonine
519-09-5

benzylecgonine

(1R,2R,3S,5S)-2-((6-(benzyloxy)-6-oxohexyl)carbamoyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate

(1R,2R,3S,5S)-2-((6-(benzyloxy)-6-oxohexyl)carbamoyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate

Conditions
ConditionsYield
Stage #1: 6-amino-hexanoic acid benzyl ester toluene-4-sulfonic acid; benzylecgonine With dmap In dichloromethane for 1.5h; Inert atmosphere; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 96h; Inert atmosphere;		71%
t-butyl (RS)-phenylalaninate
16367-71-8

t-butyl (RS)-phenylalaninate

benzylecgonine
519-09-5

benzylecgonine

Benzoic acid (1R,2R,3S,5S)-2-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Benzoic acid (1R,2R,3S,5S)-2-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Conditions
ConditionsYield
With benzotriazol-1-yl-oxy-tris-pyrrolidinophosphonium; triethylamine In dichloromethane for 12h; Ambient temperature;65%
ethanol
64-17-5

ethanol

benzylecgonine
519-09-5

benzylecgonine

cocaethylene
529-38-4

cocaethylene

Conditions
ConditionsYield
Stage #1: benzylecgonine With oxalyl dichloride at 20℃; for 0.333333h;
Stage #2: ethanol at 20℃; for 12h;		60%
With hydrogenchloride
With hydrogenchloride at 0℃; for 48h;
diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

benzylecgonine
519-09-5

benzylecgonine

A

Benzoic acid (1R,2R,3S,5S)-2-(N,N'-diisopropyl-carbamimidoyloxycarbonyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Benzoic acid (1R,2R,3S,5S)-2-(N,N'-diisopropyl-carbamimidoyloxycarbonyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

B

Benzoic acid (1R,2R,3S,5S)-2-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Benzoic acid (1R,2R,3S,5S)-2-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Conditions
ConditionsYield
With t-butyl (RS)-phenylalaninate In dichloromethane Ambient temperature;A 58%
B 15%
...Expand
t-butyl (RS)-phenylalaninate
16367-71-8

t-butyl (RS)-phenylalaninate

benzylecgonine
519-09-5

benzylecgonine

(S)-N-benzoylphenylalanine tert-butyl ester
109309-90-2

(S)-N-benzoylphenylalanine tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;34%
benzylecgonine
519-09-5

benzylecgonine

3β-(benzoyloxy)-2β-(hydroxymethyl)-8-methyl-8-azabicyclo<3.2.1>octane
137718-56-0

3β-(benzoyloxy)-2β-(hydroxymethyl)-8-methyl-8-azabicyclo<3.2.1>octane

Conditions
ConditionsYield
With B2H6-THF In tetrahydrofuran at 0 - 20℃; for 3h;31%
methanol
67-56-1

methanol

benzylecgonine
519-09-5

benzylecgonine

Cocaine
50-36-2

Cocaine

Conditions
ConditionsYield
With hydrogenchloride
Isobutyl iodide
513-38-2

Isobutyl iodide

benzylecgonine
519-09-5

benzylecgonine

(1R)-3exo-benzoyloxy-tropane-2exo-carboxylic acid isobutyl ester

(1R)-3exo-benzoyloxy-tropane-2exo-carboxylic acid isobutyl ester

Conditions
ConditionsYield
With 2-methyl-propan-1-ol at 95℃; im Rohr;
1-iodo-propane
107-08-4

1-iodo-propane

benzylecgonine
519-09-5

benzylecgonine

RTI 13
64091-46-9

RTI 13

Conditions
ConditionsYield
With propan-1-ol at 95℃; im Rohr;
ethylene dibromide
106-93-4

ethylene dibromide

benzylecgonine
519-09-5

benzylecgonine

3-benzoyloxy-tropane-2-carboxylic acid-(2-bromo-ethyl ester)

3-benzoyloxy-tropane-2-carboxylic acid-(2-bromo-ethyl ester)

Conditions
ConditionsYield
With ethanol at 95℃; im Rohr; O-benzoyl-l-ecgonine-<β-bromo-ethyl ester>;
benzylecgonine
519-09-5

benzylecgonine

methyl iodide
74-88-4

methyl iodide

Cocaine
50-36-2

Cocaine

Conditions
ConditionsYield
With methanol at 100℃; im Rohr;
With methanol; sodium methylate at 100℃; im Rohr;
benzylecgonine
519-09-5

benzylecgonine

(+)-pseudoecgonine
481-38-9

(+)-pseudoecgonine

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide
benzylecgonine
519-09-5

benzylecgonine

ecgonine
481-37-8

ecgonine

Conditions
ConditionsYield
With hydrogenchloride
benzylecgonine
519-09-5

benzylecgonine

2-β-benzamido-3β-tropanol

2-β-benzamido-3β-tropanol

Conditions
ConditionsYield
With thionyl chloride Behandeln des Reaktionsprodukts mit NaN3 in H2O, Erwaermen mit wss. HCl und anschliessendes Behandeln mit wss. NaOH;
benzylecgonine
519-09-5

benzylecgonine

benzoylnorecgonine
41889-45-6

benzoylnorecgonine

Conditions
ConditionsYield
With potassium permanganate; sodium carbonate
2-(4-nitrophenyl)ethanol
100-27-6

2-(4-nitrophenyl)ethanol

benzylecgonine
519-09-5

benzylecgonine

3β-(benzoyloxy)-8-methyl-8-azabicyclo<3.2.1>octane-2β-carboxylic acid (p-nitrophenyl)ethyl ester
137819-59-1

3β-(benzoyloxy)-8-methyl-8-azabicyclo<3.2.1>octane-2β-carboxylic acid (p-nitrophenyl)ethyl ester

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, RT, 6 h, 2.) acetone, reflux, 3 h; Yield given. Multistep reaction;
2-phenylethanol
60-12-8

2-phenylethanol

benzylecgonine
519-09-5

benzylecgonine

RTI 53
137718-50-4

RTI 53

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, RT, 6 h, 2.) acetone, reflux, 3 h; Yield given. Multistep reaction;
methylamine
74-89-5

methylamine

benzylecgonine
519-09-5

benzylecgonine

3β-(benzoyloxy)-8-methyl-8-azabicyclo<3.2.1>octane-2β-carboxylic acid N-methylamide
137819-57-9

3β-(benzoyloxy)-8-methyl-8-azabicyclo<3.2.1>octane-2β-carboxylic acid N-methylamide

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, RT, 1 h, 2.) CH2Cl2, 3 h; Yield given. Multistep reaction;
benzyl alcohol
100-51-6

benzyl alcohol

benzylecgonine
519-09-5

benzylecgonine

RTI 52
137718-48-0

RTI 52

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, RT, 6 h, 2.) acetone, reflux, 3 h; Yield given. Multistep reaction;
benzylecgonine
519-09-5

benzylecgonine

benzoylecgonine acid chloride
61194-36-3

benzoylecgonine acid chloride

Conditions
ConditionsYield
With thionyl chloride
With thionyl chloride at 0℃; for 4h;
With oxalyl dichloride In dichloromethane for 1h; Ambient temperature;
With oxalyl dichloride for 0.25h; Substitution;

8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 3-(benzoyloxy)-8-methyl-, (1R,2R,3S,5S)- Specification

The 8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 3-(benzoyloxy)-8-methyl-, (1R,2R,3S,5S)-, with the CAS registry number 519-09-5 and EINECS registry number 208-263-5, has the systematic name of (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid. It belongs to the following product categories: Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; Alkaloids Alphabetic; BA-BHDrugs of Abuse; Drugs of Abuse; Ecgoninen Forensic and Veterinary Standards; Neat Compounds; B; Chemical Structure; Drugs & Metabolites; Solutions. And the molecular formula of the chemical is C16H19NO4.

The characteristics of 8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 3-(benzoyloxy)-8-methyl-, (1R,2R,3S,5S)- are as followings: (1)ACD/LogP: 2.26; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1.279; (6)ACD/KOC (pH 7.4): 1.281; (7)#H bond acceptors: 5; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 66.84 Å2; (11)Index of Refraction: 1.599; (12)Molar Refractivity: 76.273 cm3; (13)Molar Volume: 223.117 cm3; (14)Polarizability: 30.237×10-24cm3; (15)Surface Tension: 56.314 dyne/cm; (16)Density: 1.297 g/cm3; (17)Flash Point: 221.38 °C; (18)Enthalpy of Vaporization: 73.766 kJ/mol; (19)Boiling Point: 442.439 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)O
(2)InChI: InChI=1/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1
(3)InChIKey: GVGYEFKIHJTNQZ-RFQIPJPRBD

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