92138-20-0|(5R,9R,Z)-5-Amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one| Ambeed

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Quality Control of [ 92138-20-0 ] Purity: 97% SDS Specification

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Product Details of [ 92138-20-0 ]

CAS No. :	92138-20-0
Formula :	C₁₅H₁₈N₂O
M.W :	242.32
SMILES Code :	O=C1C=CC([C@@](/C2=C\C)(N)CC(C)=C[C@@]2([H])C3)=C3N1
MDL No. :	MFCD28344104

Safety of [ 92138-20-0 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H300-H310-H315-H319-H330-H335
Precautionary Statements:	P260-P264-P280-P284-P301+P310-P302+P350
Class:	6.1
UN#:	1544
Packing Group:	Ⅱ

Application In Synthesis of [ 92138-20-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 92138-20-0 ]

[ 92138-20-0 ] Synthesis Path-Downstream 1~35

1
[ 50-00-0 ]
[ 64-18-6 ]
[ 92138-20-0 ]
[ 103526-54-1 ]

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 837 - 840.

2
[ 92138-20-0 ]
[ 3279-76-3 ]

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 837 - 840.

3
[ 92138-20-0 ]
[ 103526-52-9 ]

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 837 - 840.

4
[ 92138-20-0 ]
[ 103526-51-8 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform methanol; ethanol;	EXAMPLE 8 Preparation of (5R,9R)-5-amino-11-ethyl-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one Hydrogenation of Huperzine A (150 mg.) in the presence of platinum oxide (60 mg.) in ethanol (20 ml.) gave the title dihydrohuperzine A, where the former exo-double bond is saturated. This material was purified by silica gel column chromatography (chloroform-methanol, 15:1 as solvent) followed by recrystallization from methanol-acetone (yield 100 mg). m.p. 269-270 C. MS 244 (M+).

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 837 - 840.
[2]Patent: US5177082,1993,A .

5
[ 92138-20-0 ]
[ 103526-51-8 ]

References: [1]Canadian Journal of Chemistry,1989,vol. 67,p. 1538 - 1540.

6
[ 92138-20-0 ]
[ 108-24-7 ]
[ 103548-81-8 ]

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 837 - 840.

7
[ 120686-04-6 ]
[ 92138-20-0 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 4695 - 4696.

8
[ 92138-20-0 ]
[ 1885-14-9 ]
[ 957115-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	EXAMPLE 1; O,N-Bis(phenoxycarbonyl)huperzine A; 242 mg (1.00 mmol) (-)-huperzine A and 0.52 mL (3.00 mmol) N,N-diisopropylethylamine in 10 mL of dichloromethane were added 0.38 mL (3.00 mmol) phenyl chloroformate. The resulting mixture was stirred overnight at room temperature. The reaction mixture was worked up and the crude product was purified using silica gel chromatography with ethyl acetate-hexane (1:1) as an eluent to obtain the titled compound as a glassy material. 1H NMR (CDCl3, 500 MHz)delta 7.91 (d, 1H, J=8 Hz, Pyridine-H), 7.59-6.88 (m, 10H, phenyl-H), 6.81 (d, 1H, J=8 Hz, Pyridine-H), 5.53 (q, 1H, J=6.5 Hz, vinyl-H), 5.43 (br d, 1H, J=5 Hz, vinyl-H), 3.68-1.51 (m, 11H, other H).

References: [1]Patent: US2007/270454,2007,A1 .Location in patent: Page/Page column 3-4.

9
[ 185741-40-6 ]
[ 92138-20-0 ]

References: [1]Tetrahedron,1998,vol. 54,p. 5471 - 5484.
[2]Tetrahedron,1998,vol. 54,p. 5471 - 5484.

10
[ 185741-49-5 ]
[ 92138-20-0 ]

References: [1]Tetrahedron,1998,vol. 54,p. 5471 - 5484.
[2]Tetrahedron,1998,vol. 54,p. 5471 - 5484.

11
[ 134875-91-5 ]
[ 92138-20-0 ]

References: [1]Tetrahedron,1998,vol. 54,p. 5471 - 5484.

12
[ 191607-29-1 ]
[ 92138-20-0 ]

References: [1]Tetrahedron,1998,vol. 54,p. 5471 - 5484.

13
[ 185741-44-0 ]
[ 92138-20-0 ]

References: [1]Tetrahedron,1998,vol. 54,p. 5471 - 5484.

14
[ 185741-41-7 ]
[ 92138-20-0 ]

References: [1]Tetrahedron,1998,vol. 54,p. 5471 - 5484.
[2]Tetrahedron,1998,vol. 54,p. 5471 - 5484.

15
[ 185741-42-8 ]
[ 92138-20-0 ]

References: [1]Tetrahedron,1998,vol. 54,p. 5471 - 5484.
[2]Tetrahedron,1998,vol. 54,p. 5471 - 5484.

16
[ 134781-04-7 ]
[ 92138-20-0 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 4695 - 4696.

17
[ 134287-26-6 ]
[ 92138-20-0 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 4695 - 4696.

18
[ 92138-20-0 ]
[ 103526-54-1 ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; formic acid;	EXAMPLE 4 Preparation of (5R, 9R, 11E)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5-(dimethylamino)-5,9-methanocycloocta[b]pyridin-2(1H)-one The di-methyl derivative of Huperzine A was obtained by the treatment of Huperzine A (150 mg.) with formic acid (88%, 1 ml.) and formaldehyde (35%, 1 ml.) at 100 C. for 4 hours. After concentrating under reduced pressure and basifying with conc. ammonium hydroxide, the desired product was extracted with chloroform. Recrystallization from a chloroform-methanol mixture gave pure title compound (yield 150 mg.). mp 243-245 C. MS 270 (M+).

References: [1]Patent: US5177082,1993,A .

19
[ 92138-20-0 ]
[ 103526-55-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; dimethyl sulfate; In chloroform; acetone;	EXAMPLE 5 Preparation of (5R, 9R, 11E)-11-ethylidene-5,6,9,10-tetrahydro-1,7-dimethyl-5-(dimethylamino)-5,9-methanocycloocta[b]pyridin-2(1H)-one The title trimethyl derivative of Huperzine A was obtained by methylation of Huperzine A (150 mg.) with dimethyl sulfate (3 ml.) in acetone (10 ml.) and 20% aqueous sodium hydroxide (4 ml.) at reflux. After three (3) hours, the mixture was extracted with chloroform. TLC analysis of this extract showed two spots. Purification by silica gel column chromatography (chloroform as solvent, impurity being eluted first) gave the trimethyl derivative as an oil (yield 110 mg.). The title compound is an oil. MS 284 (M+).

References: [1]Patent: US5177082,1993,A .

20
[ 92138-20-0 ]
(5R,9R)-5-amino-11-ethyl-5,6,7,8,9,10-hexahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	acetic acid;	EXAMPLE 9 Preparation of (5R,9R)-5-amino-11-ethyl-5,6,7,8,9,10-hexahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one Huperzine A (200 mg.) was hydrogenated in the presence of platinum oxide (100 mg.) and acetic acid (10 ml.). After basification and extraction into chloroform, the title tetrahydrohuperzine A was recrystallized from a methanol-acetone mixture (yield 180 mg.). m.p. 264-5 C. MS 246 (M+).

References: [1]Patent: US5177082,1993,A .

21
[ 92138-20-0 ]
N-acetyl Huperzine A [ No CAS ]
[ 103548-81-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; acetic anhydride; In chloroform methanol;	EXAMPLE 10 Preparation of (5R, 9R, 11E)-5-(acetylamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one The titled N-acetyl Huperzine A derivative was prepared by treating Huperzine A (100 mg.) with acetic anhydride (1 ml.) and pyridine (0.5 ml.) at room temperature for one week. This mixture was poured into ice-water and extracted with chloroform. The chloroform extract was concentrated and purified by silica gel column chromatography (chloroform-methanol, 15:1 as solvent) and recrystallization from acetone (yield 100 mg.). m.p. 276-7 C. MS 284 (M+).

References: [1]Patent: US5177082,1993,A .

Yield	Reaction Conditions	Operation in experiment
20 g (59%)		EXAMPLE I Synthesis of Huperzine A Preparation of lactam 2 (n=1) In a 500 mL round-bottomed flask equipped with a water separator and a condenser were placed 25 g (0.16 mol) of 1,4-cyclohexanedione monoethylene ketal, 27 mL (0.32 mol) of pyrrolidine, 1 g of p-toluenesulphonic acid, and 250 mL of benzene. The mixture was refluxed until no more water separated in the water separator. Benzene was evaporated and the residue was dissolved in 250 mL of dioxane. To this solution was added 34 g (0.48 mol) of acrylamide and the mixture was refluxed overnight. Water (100 mL) was added and the solution was refluxed for 12 h. After cooling down to room temperature, the dioxane was removed by rotary evaporation and the aqueous residue was extracted with CHCl1. The extracts were washed with brine, dried with anhydrous MgSO4, and filtered. After evaporation of the solvent, the residue was chromatographed on silica gel with ethyl acetate as the eluent. The yield was 20 g (59%).
4 mg (70%)		Huperzine A Iodotrimethylsilane (50 muM, 0.35 mmol) was added dropwise to a solution of the carbamate 10 (7 mg, 0.02 mmol) in 2 mL of chloroform under nitrogen at room temperature. The solution was then refluxed overnight. Methanol (2 mL) was added, and the solution was refluxed for an additional 2 h. Concentration and flash chromatography on silica gel half-saturated with ammonia (3% methanol in chloroform) gave 4 mg (70%) of huperzine A along with 2 mg (30%) of the partially deprotected carbamate.
		Example 6 Concurrent Deprotection and Double Bond Rearrangement of a Compound of Formula 54-E, Wherein Y is -NHR2 and R2 is Tert-butyloxycarbonyl to Give Huperzine A (1) Iodotrimethylsilane (about 4 equivalents) is added drop-wise at a rate of about 20 to about 40 minutes per 0.05 moles to a solution of a carbamate of formula 52, wherein Y is -NH(tert-butyloxycarbonyl) (1 equivalent) in dry chloroform (about 350 to about 450 equivalents) under an inert atmosphere at room temperature. The solution is then refluxed for about 2 to about 24 hours, preferably for about 4 to about 8 hours. The resulting solution is concentrated, the residue dissolved in methanol (about 250 to about 350 equivalents) and refluxed for about 12 to about 24 hours. The volatiles are removed by evaporation, the residue dissolved in dry dioxane (about 100 to about 200 equivalents) and trifluormethansulfonic acid (about 2 equivalents) is added in one portion and the solution stirred at a temperature of about 80 to about 100 C. for about 18 to about 30 hours, preferably at about 90 C. for about 24 hours. The solvent is removed and the residue partitioned between 10% aqueous sodium bicarbonate and 10% methanol in chloroform. The organic layers are washed with brine, dried (magnesium sulfate) and concentrated. Flash chromatography on silica gel half-saturated with ammonia (3% methanol in chloroform) gives huperzine A (1). The structure of the product is confirmed by 1H NMR and mass spectroscopy.

23
[ 92138-20-0 ]
[ 541-41-3 ]
[ 123436-03-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0℃; for 4h;	Dissolved 10 mg huperzine A and 10 mg triethylamine in 5 mL dry THF; cooled the solution down to 0 C.; added ethyl chlorocarbonate (6 mg) and stirred the resultant reaction mixture for 4 hours; filtered to remove solid residues; after concentrating the filtrate, purified on prep TLC (chloroform:methanol=9:1) to yield 8 mg of pure title compound. MS:315(M+1).

References: [1]Patent: US2008/119506,2008,A1 .Location in patent: Page/Page column 4.

24
[ 92138-20-0 ]
[ 121-33-5 ]
[ 923272-87-1 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; for 3h;Heating / reflux;	Added 10 mg huperzine A and 8 mg vanillin in 5 mL isopropanol; stirred at reflux for 3 hours; stripped solvent in vacuo to yield 16 mg product. MS:377(M+1).

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6937 - 6941.
[2]Patent: US2008/119506,2008,A1 .Location in patent: Page/Page column 5.

25
[ 50-00-0 ]
[ 92138-20-0 ]
[ 103526-53-0 ]

Yield	Reaction Conditions	Operation in experiment
		Huperzine A 10 mg, and 37% aqueous solution of formaldehyde were refluxed for 1 hour in 2 mL of isopropanol; the solvent was stripped in vacuo; THF (dry, 5 mL) and NaBH(OOCCH3)3 0.15 g were added, the reaction mixture was allowed to stir for 4 hours; and then filtered to remove solid substances. The filtrate was purified after concentrating on prep TLC (chloroform:methanol=9:1) to yield 6 mg of pure title compound. MS:257 (M+1).

References: [1]Patent: US2008/119506,2008,A1 .Location in patent: Page/Page column 4.

26
[ 92138-20-0 ]
[ 104-55-2 ]
[ 955117-18-7 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; for 3h;Heating / reflux;	Example 2 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 20 mg Huperzine A, and 77 mg cinnamaldehyde were refluxed in 2 mL isopropanol for 3 hours. Solvent was removed under vacuum. The crude reaction mixture was dissolved in 3 mL anhydrous THF and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H).
	In isopropyl alcohol; for 3h;Heating / reflux;	Example 2 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 20 mg of Huperzine A, 77 mg of cinnamaldehyde were refluxed in 2 mL of isopropanol for 3 hours, and then solvent was removed under vacuum, 3 mL of anhydrous THF added and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H).

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6937 - 6941.
[2]Patent: US2009/118320,2009,A1 .Location in patent: Page/Page column 17.
[3]Patent: EP2044937,2009,A1 .Location in patent: Page/Page column 16-17.

27
[ 955117-18-7 ]
[ 92138-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	With artificial gastric fluid; for 0.25 - 3.83333h;Conversion of starting material;	Studies of the release of Huperzine A by H064-5-2 (title compound of Example 2, (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one) in artificial gastric fluidInstruments and ReagentsHPLC: Shimadzu SCL-10Avp, LC-10Atvp pump, SPD-M10Avp, DGU-14A. UV-VIS spectrophotometer: SHIMADZU UV-260. Huperzine A check sample (purity 99%). H064-5-2 (title compound of Example 2, (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one): prepared by Tianjin Hemay BioTech Co. Ltd). Methanol (chromatographic grade). Purified H2O. All other reagents are analytically pure.Experiment and Results1) Determination of wavelength: 1 mg cinnamaldehyde, 1 mg H064-5-2 and 1 mg Huperzine A check sample were precisely measured out. Methanol was then added to obtain a constant volume of 10 mL. 0.5 mL solution was subsequently taken out from the original solution to obtain a constant volume of 10 mL by adding methanol. Samples were scanned at 190-500 nm to identify absorption with methanol as blank. The results are the following: absorption peaks of H064-5-2 are 204.4 nm and 286.8 nm. The absorption peaks of cinnamaldehyde are 205.8 nm, 210.6 nm, 223.2 nm and 285.0 nm. The absorption peaks of huperzine A are 202.2 nm, 228.6 nm, 311.0 nm, 354.2 nm and 373.6 nm.Conclusion: H064-5-2 has characteristic absorption peak at 287 nm.2) Chromatography conditions: C18 (150×4.6 mm, 5 mum), methanol/water (1:1) as mobile phase containing 0.02% triethanolamine. Flow rate 1 mL/min. Detection conditions are the following: detector: SPD-M10Avp. Detection wavelength: 287 nm. Injected sample volume: 20 mul.3) Blank test: 0.3 mL grastric fluid was extracted, and 5 mL methanol was added to obtain a constant volume, injected sample volume is 20 mul, there are no peaks appearing at the retention times of the control sample.4) Chromatogram of Huperzine A:A) 1.0 mg Huperzine A check sample was precisely measured and added in a 10 mL volumetric flask; methanol was added to obtain a constant volume. 0.05 mL was then precisely extracted and 10 mL methanol was added to obtain a 10 mL constant volume, the injected sample volume is 20 mul. The chromatogram was recored.B) 1.0 mg Huperzine A check sample was precisely measured and added in a 10 mL volumetric flask, gastric fluid was added to get a constant volume. 0.05 mL was taken out and methanol was added to get a constant volume of 10 mL with 0.5 ng/mul. The injected sample volume is 20 mul. Chromatogram was recorded.5) Chromatogram of cinnamaldehyde: a small volume of cinnamaldehyde check sample was dissolved in methanol, and its chromatogram was recorded.6) Standard curve: 1.0 mg Huperzine A check sample was precisely measured and added into a 10 mL volumetric flask, methanol was added to get a constant volume. 0.05 mL was taken out and methanol was added to it to get a constant volume of 10 mL, the concentration of which is 0.5 ng/mul. 2, 4, 5, 10, 25, and 50 mul solution were separately taken out, and injected according to the above stated chromatographic conditions. After linear regression analysis, the standard curve was plotted with the injected volume (ng) of huperzine A check sample as Y-axis, the area of main peak as x-axis. The results are shown in the Table 1; 7) Sample measurement: 1.0 mg H064-5-2 sample was precisely measured, dissolved in gastric fluid with 2 min ultrasound; a constant volume of 10 mL with the concentration of 0.1 mg/mL was then obtained. 0.03 mL was precisely extracted at prescribed times, and methanol was added to get a constant volume of 5 mL, which was measured. The main peak area of Huperzine A was recorded, and the concentration was determined to be 0.6 ng/mul. The injected sample volume was 20 mul (12 ng). The results are listed in Table 2 and in FIG. 1.

References: [1]Patent: US2009/118320,2009,A1 .Location in patent: Page/Page column 19-20.

28
[ 121-32-4 ]
[ 92138-20-0 ]
[ 956291-33-1 ]