CAS No.27773-65-5,(3alpha,16alpha)-eburnamenine-14-carboxylic acid Suppliers

Products Categories

Pharmaceutical (9)
Others (7)
Organic Chemicals (6)

Basic Information

Molecular Structure:
CAS No.:	27773-65-5
Name:	(3alpha,16alpha)-eburnamenine-14-carboxylic acid
Article Data:	10

Formula:	C20H22 N2 O2
Molecular Weight:	322.407
Synonyms:	Apovincamin-22-oicacid (8CI); Eburnamenine-14-carboxylic acid, (3a,16a)- (9CI); 1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine,eburnamenine-14-carboxylic acid deriv.; (+)-Apovincaminic acid;(+)-cis-Apovincaminic acid; (3a,16a)-Eburnamenine-14-carboxylicacid; Apovincaminic acid; cis-Apovincaminic acid
Density:	1.38±0.1 g/cm3(Predicted)
Melting Point:	126-129 °C
Boiling Point:	429.9±45.0 °C(Predicted)
PSA:	45.47000
LogP:	3.60770

Synthetic route

: 42971-09-5
Vinpocetine

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 80℃; for 2h;	98%
With sodium hydroxide In ethanol for 5h; Reflux;	92.4%
With sodium hydroxide In methanol at 40℃; for 1h; Kinetics; Further Variations:; Reagents; Solvents; Temperatures; pH-values;

: 4880-92-6
apovincamine

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 3h; Reflux;	96%
With sodium hydroxide In ethanol at 20℃; for 2h; Reflux;	96%
With sodium hydroxide In tetrahydrofuran; methanol for 12h;
With hydrogenchloride at 20 - 37℃; for 2h; object of study: degree of hydrolysis;
With sodium hydroxide at 65℃; for 2h;

: 78101-34-5
MR-711

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
With hydrogenchloride at 20 - 37℃; for 2h; object of study: degree of hydrolysis;
With esterases of rat plasma; water at 37℃; object of study: rate of hydrolysis;

: 42971-09-5
Vinpocetine

A: 27773-65-5
Apovincaminic acid

B: 40163-56-2
14,15-dihydro-14β-hydroxy-(3α,16α)-eburnamenine-14-carboxylic acid ethyl ester

C: 3α-epivincaminic acid ethyl ester

D: 14-epivincaminic acid

E: 4880-88-0
vinburnine

F: 28152-73-0
(3α,14β,16α)-14,15-dihydro-14-hydroxyeburnamenine-14-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride at 80℃; for 336h; Product distribution; Rate constant; Thermodynamic data; ln A, Ea, ΔS<*>; degradation of vinpocetine in aqueous solutions, degradation products equilibria in solutions, effect of various pH, temperature and ionic strength, buffer catalysis, metal ion catalysis, oxygen effect, mechanism;

...Expand

: 3389-21-7
3-(2-bromoethyl)-1H-indole

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 80 percent / NaHCO3 / acetonitrile / 24 h / Heating 2: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr 3: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h 4: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h 5: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 6: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 7: Et3N / CH2Cl2 / 0.5 h / 0 °C 8: 55 percent / DBU / 1 h / 100 °C 9: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme
Multi-step reaction with 10 steps 1: 80 percent / NaHCO3 / acetonitrile / 24 h / Heating 2: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr 3: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h 4: 46 percent / TFA / 24 h / Heating 5: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h 6: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 7: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 8: Et3N / CH2Cl2 / 0.5 h / 0 °C 9: 55 percent / DBU / 1 h / 100 °C 10: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme

Yield

Multi-step reaction with 9 steps
1: 80 percent / NaHCO3 / acetonitrile / 24 h / Heating
2: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr
3: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h
4: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h
5: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h
6: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C
7: Et3N / CH2Cl2 / 0.5 h / 0 °C
8: 55 percent / DBU / 1 h / 100 °C
9: aq. NaOH / methanol; tetrahydrofuran / 12 h
View Scheme

Multi-step reaction with 10 steps
1: 80 percent / NaHCO3 / acetonitrile / 24 h / Heating
2: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr
3: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h
4: 46 percent / TFA / 24 h / Heating
5: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h
6: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h
7: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C
8: Et3N / CH2Cl2 / 0.5 h / 0 °C
9: 55 percent / DBU / 1 h / 100 °C
10: aq. NaOH / methanol; tetrahydrofuran / 12 h
View Scheme

: 95407-25-3, 95407-56-0
1-phenylpropyl (2S,3R)-3-cyano-3-ethylpipecolate

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 80 percent / NaHCO3 / acetonitrile / 24 h / Heating 2: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr 3: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h 4: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h 5: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 6: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 7: Et3N / CH2Cl2 / 0.5 h / 0 °C 8: 55 percent / DBU / 1 h / 100 °C 9: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme
Multi-step reaction with 10 steps 1: 80 percent / NaHCO3 / acetonitrile / 24 h / Heating 2: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr 3: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h 4: 46 percent / TFA / 24 h / Heating 5: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h 6: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 7: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 8: Et3N / CH2Cl2 / 0.5 h / 0 °C 9: 55 percent / DBU / 1 h / 100 °C 10: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme

Yield

: 95407-55-9
(2S,3R)-3-Cyano-3-ethyl-1-[2-(1H-indol-3-yl)-ethyl]-piperidine-2-carboxylic acid

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h 2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h 3: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 4: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 5: Et3N / CH2Cl2 / 0.5 h / 0 °C 6: 55 percent / DBU / 1 h / 100 °C 7: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme
Multi-step reaction with 8 steps 1: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h 2: 46 percent / TFA / 24 h / Heating 3: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h 4: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 5: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 6: Et3N / CH2Cl2 / 0.5 h / 0 °C 7: 55 percent / DBU / 1 h / 100 °C 8: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme

Yield

Multi-step reaction with 7 steps
1: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h
2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h
3: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h
4: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C
5: Et3N / CH2Cl2 / 0.5 h / 0 °C
6: 55 percent / DBU / 1 h / 100 °C
7: aq. NaOH / methanol; tetrahydrofuran / 12 h
View Scheme

Multi-step reaction with 8 steps
1: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h
2: 46 percent / TFA / 24 h / Heating
3: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h
4: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h
5: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C
6: Et3N / CH2Cl2 / 0.5 h / 0 °C
7: 55 percent / DBU / 1 h / 100 °C
8: aq. NaOH / methanol; tetrahydrofuran / 12 h
View Scheme

: 95464-02-1
(3R*,4S*,14R*,15R*,16S*)-14,15-dihydro-15-hydroxy-14-methoxycarbonyleburnamenine

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 0.5 h / 0 °C 2: 55 percent / DBU / 1 h / 100 °C 3: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme

: 95407-51-5
1-cyano-1-ethyl-12-<(methoxycarbonyl)methyl>-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 2: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 3: Et3N / CH2Cl2 / 0.5 h / 0 °C 4: 55 percent / DBU / 1 h / 100 °C 5: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme

: 95407-50-4, 95407-59-3
1-phenylpropyl (2S,3R)-3-cyano-3-ethyl-N-<2-(3-indolyl)ethyl>pipecolate

: 27773-65-5
Apovincaminic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr 2: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h 3: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h 4: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 5: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 6: Et3N / CH2Cl2 / 0.5 h / 0 °C 7: 55 percent / DBU / 1 h / 100 °C 8: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme
Multi-step reaction with 9 steps 1: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr 2: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h 3: 46 percent / TFA / 24 h / Heating 4: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h 5: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h 6: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C 7: Et3N / CH2Cl2 / 0.5 h / 0 °C 8: 55 percent / DBU / 1 h / 100 °C 9: aq. NaOH / methanol; tetrahydrofuran / 12 h View Scheme

Yield

Multi-step reaction with 8 steps
1: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr
2: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h
3: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h
4: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h
5: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C
6: Et3N / CH2Cl2 / 0.5 h / 0 °C
7: 55 percent / DBU / 1 h / 100 °C
8: aq. NaOH / methanol; tetrahydrofuran / 12 h
View Scheme

Multi-step reaction with 9 steps
1: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr
2: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h
3: 46 percent / TFA / 24 h / Heating
4: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h
5: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h
6: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C
7: Et3N / CH2Cl2 / 0.5 h / 0 °C
8: 55 percent / DBU / 1 h / 100 °C
9: aq. NaOH / methanol; tetrahydrofuran / 12 h
View Scheme

Downstream Products

4880-88-0