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Basic Information

Molecular Structure:
CAS No.:	485-64-3
Name:	(8alpha,9R)-10,11-dihydrocinchonan-9-ol

Formula:	C19H24 N2 O
Molecular Weight:	296.412
Synonyms:	Hydrocinchonidine(6CI,7CI,8CI); (-)-Dihydrocinchonidine; (-)-Hydrocinchonidine;10,11-Dihydrocinchonidine; Cinchamidine; Dihydrocinchonidine
Density:	1.18g/cm³
Melting Point:	230°
Boiling Point:	467.1°Cat760mmHg
Flash Point:	236.3°C
PSA:	36.36000
LogP:	3.32650

Synthetic route

: 485-71-2
Cinchonidin

: 485-64-3
(-)-hydrocinchonidine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 10h;	92%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 12h;	86%
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 24h; Reagent/catalyst; Green chemistry; chemoselective reaction;	83%

: 5962-19-6
(8α,9R)-10,11-dihydro-cinchonan-6',9-diol

: 485-64-3
(-)-hydrocinchonidine

: 109922-61-4, 109959-06-0
1-[(3R,4S)-3-Ethyl-4-(3-quinolin-4-yl-oxiranylmethyl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone

A: 485-65-4
dihydrocinchonine

B: 485-64-3
(-)-hydrocinchonidine

Conditions

Conditions	Yield
With potassium carbonate 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h; Yield given. Multistep reaction. Yields of byproduct given;

dihydrocinchoninone: dihydrocinchoninone

: 485-64-3
(-)-hydrocinchonidine

Conditions

Conditions	Yield
With sodium ethanolate; aluminium
With sodium ethanolate; zinc
With sodium ethanolate; aluminium
With sodium ethanolate; zinc

hydrocinchoninone: hydrocinchoninone

A: 485-65-4
dihydrocinchonine

B: 485-64-3
(-)-hydrocinchonidine

Conditions

Conditions	Yield
With ethanol; palladium Hydrogenation;

: 71-41-0
pentan-1-ol

: 485-65-4
dihydrocinchonine

KOH: KOH

A: 73522-74-4
hydrocinchonine

B: 485-64-3
(-)-hydrocinchonidine

C: 73522-73-3
hydrocinchonidine

...Expand

: 485-65-4
dihydrocinchonine

A: 485-64-3
(-)-hydrocinchonidine

B (9R)-10,11-dihydro-cinchonan-9-ol, epihydrocinchonidine: (9R)-10,11-dihydro-cinchonan-9-ol, epihydrocinchonidine

Conditions

Conditions	Yield
With potassium hydroxide; pentan-1-ol

: 491-35-0
C6H4NCH2CHCCH2

: 485-64-3
(-)-hydrocinchonidine

Conditions

Yield

Multi-step reaction with 6 steps
1: lithium diisopropylamide, pyridine hydrochloride
2: 90 percent / pyridine hydrochloride / methanol; pyridine; various solvent(s) / 36 h / Ambient temperature
3: 1) water 2.) NH4OAc, NaCNBH3 / 1) β-glucosidase / 2.) pH=6.2, 18 h
4: 1.) 3percent HCl, 2.) NaCNBH3 / 1.) aq MeOH, reflux, 40 min
5: 2.) CF3CO3H, Na2HPO4 / 1.) 0 grad C, 2.) CH2Cl2, rt, 12 h
6: 1.) K2CO3 / 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h
View Scheme

: 109922-57-8
[4]quinolyl-acetic acid

: 485-64-3
(-)-hydrocinchonidine

Conditions

Yield

Multi-step reaction with 5 steps
1: 90 percent / pyridine hydrochloride / methanol; pyridine; various solvent(s) / 36 h / Ambient temperature
2: 1) water 2.) NH4OAc, NaCNBH3 / 1) β-glucosidase / 2.) pH=6.2, 18 h
3: 1.) 3percent HCl, 2.) NaCNBH3 / 1.) aq MeOH, reflux, 40 min
4: 2.) CF3CO3H, Na2HPO4 / 1.) 0 grad C, 2.) CH2Cl2, rt, 12 h
5: 1.) K2CO3 / 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h
View Scheme

: 109922-60-3
4-[(E)-3-((3R,4R)-3-Ethyl-piperidin-4-yl)-propenyl]-quinoline

: 485-64-3
(-)-hydrocinchonidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) CF3CO3H, Na2HPO4 / 1.) 0 grad C, 2.) CH2Cl2, rt, 12 h 2: 1.) K2CO3 / 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h View Scheme

485-64-3

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