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64744-50-9

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64744-50-9 Usage

Description

Gabapentin-lactam is a neuroprotective compound that reduces protein aggregates and improves motor performance in a transgenic mouse model of Huntington's disease. It displays neurotrophic effects, enhancing the formation of dendritic filopodia and inducing a network of F-actin-containing neurites in cultured hippocampal neurons. Additionally, it promotes the survival of cultured central nervous system neurons possibly by opening mitochondrial KATP channels and displays neuroprotective effects in a rat model of acute retinal ischemia.

Uses

Used in Pharmaceutical Applications:
Gabapentin-lactam is used as a neuroprotective agent for reducing protein aggregates and improving motor performance in a transgenic mouse model of Huntington's disease. It opens mitochondrial ATP-dependent potassium channels, which may contribute to its neuroprotective effects.
Used in Analytical Applications:
Gabapentin-lactam is used as a secondary standard in several analytical applications, including but not limited to pharmaceutical release testing, pharmaceutical method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements. These secondary standards are qualified as Certified Reference Materials, ensuring accurate and reliable results in various industries.

References

1) Zucker et al. (2004), Gabapentin-lactam, but not gabapentin, reduces protein aggregates and improves motor performance in transgenic mouse model of huntington’s disease; Nauyn Schmiedebergs Arch. Pharmacol., 370 131 2) Henle et al. (2006), Gabapentin-lactam induces dendritic filopodia and motility in cultured hippocampal neurons; J. Pharmacol. Exp. Ther., 319 181 3) Pielen et al. (2004), Retinal ganglion cell survival is enhanced by gabapentin-lactam in vitro: evidence for involvement of mitochondrial KATP channels; Graefes Arch. Clin. Exp. Ophthalmol., 242 240 4) Lagreze et al. (2001), The neuroprotective properties of gabapentin-lactam; Graefes Arch. Clin. Exp. Ophthalmol., 239 845

Check Digit Verification of cas no

The CAS Registry Mumber 64744-50-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,7,4 and 4 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 64744-50:
(7*6)+(6*4)+(5*7)+(4*4)+(3*4)+(2*5)+(1*0)=139
139 % 10 = 9
So 64744-50-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H15NO/c11-8-6-9(7-10-8)4-2-1-3-5-9/h1-7H2,(H,10,11)

64744-50-9 Well-known Company Product Price

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  • Sigma-Aldrich

  • (PHR1322)  4,4-Pentamethylene-2-pyrrolidinone  pharmaceutical secondard standard; traceable to USP and PhEur

  • 64744-50-9

  • PHR1322-100MG

  • 1,098.28CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001281)  GabapentinimpurityA  European Pharmacopoeia (EP) Reference Standard

  • 64744-50-9

  • Y0001281

  • 1,880.19CNY

  • Detail
  • USP

  • (1287325)  GabapentinRelatedCompoundA  United States Pharmacopeia (USP) Reference Standard

  • 64744-50-9

  • 1287325-50MG

  • 14,578.20CNY

  • Detail
  • Aldrich

  • (553743)  4,4-Pentamethylene-2-pyrrolidinone  96%

  • 64744-50-9

  • 553743-25G

  • 2,468.70CNY

  • Detail

64744-50-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Gabapentin-lactam

1.2 Other means of identification

Product number -
Other names 2-AZASPIRO-(4,5)-DECAN-3-ONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:64744-50-9 SDS

64744-50-9Synthetic route

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid
99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 40℃; for 3.5h;
Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=8.2 - 8.8; Product distribution / selectivity; Heating / reflux;
100%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 50℃; for 3h;
Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=11 - 12; Product distribution / selectivity;
93.8%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide In water at 20 - 30℃; for 0.5h;
Stage #2: With sode de l'acide trichloroisocyanurique In water at 0 - 20℃; for 5h;
Stage #3: In water; toluene at 80℃; for 8h; Reagent/catalyst;
85%
Multi-step reaction with 2 steps
1.1: trichloroisocyanuric acid / methanol / 1.75 h / 20 - 25 °C
2.1: sodium hydroxide / water / 4 h / 0 - 20 °C
2.2: 8 h / 80 °C
View Scheme
(1-cyanocyclohexyl)-acetic acid
133481-09-1

(1-cyanocyclohexyl)-acetic acid

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Stage #1: (1-cyanocyclohexyl)-acetic acid With sodium hydroxide In water pH=12;
Stage #2: With hydrogen In water; toluene at 80 - 85℃; under 3750.38 - 7500.75 Torr; Inert atmosphere;
97.3%
With chromium-promoted Raney-nickel; hydrogen In water at 110℃; under 15757.7 Torr; for 9h; Reagent/catalyst; Temperature; Autoclave;95.3%
(1-cyanocyclohexyl)acetonitrile
4172-99-0

(1-cyanocyclohexyl)acetonitrile

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Stage #1: (1-cyanocyclohexyl)acetonitrile With sodium hydrogencarbonate at 25℃; for 28h; pH=7.4 - 7.5; Enzymatic reaction;
Stage #2: With sodium hydroxide In water at 20℃;
Stage #3: With hydrogen In water at 80℃; under 7500.75 Torr; Concentration; Time; Inert atmosphere;
93.63%
3-azaspiro[5,5]undecane-2,4-dione
1130-32-1

3-azaspiro[5,5]undecane-2,4-dione

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With methanol; tert-butylhypochlorite; potassium tert-butylate; potassium bromide at 60℃; for 24h; Hofmann type rearrangement; Inert atmosphere;92%
With bromine; sodium hydroxide In water at 0 - 85℃; Product distribution / selectivity;
1-(aminomethyl)cyclohexaneacetic acid potassium salt
955362-91-1

1-(aminomethyl)cyclohexaneacetic acid potassium salt

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With 4-methyl-morpholine; bis(trichloromethyl) carbonate; potassium hydroxide In water; acetonitrile at 20℃; for 0.00277778h; Inert atmosphere;92%
(1-cyanocyclohexyl)acetic acid sodium salt

(1-cyanocyclohexyl)acetic acid sodium salt

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With Raney Nickel In water at 80℃; under 7500.75 Torr; for 18h; pH=13.5;91.9%
ethyl 1-nitromethyl-1-cyclohexaneacetate
133938-45-1

ethyl 1-nitromethyl-1-cyclohexaneacetate

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
In palladium-carbon; ethanol91.6%
(+/-)-(5R,6S)-2-(benzoylamino)-4,4,6-trichloro-3-oxo-2-azaspiro[4.5]decane

(+/-)-(5R,6S)-2-(benzoylamino)-4,4,6-trichloro-3-oxo-2-azaspiro[4.5]decane

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With nickel In ethanol at 110℃; for 21h;90%
(1-cyanocyclohexyl)acetic acid barium salt

(1-cyanocyclohexyl)acetic acid barium salt

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With hydrogen In water at 80℃; under 7500.75 Torr; for 20h; pH=13.5;90%
C10H16ClNO3

C10H16ClNO3

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Stage #1: C10H16ClNO3 With sodium hydroxide In water at 0 - 20℃; for 4h;
Stage #2: In toluene at 80℃; for 8h;
90%
2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one
608532-82-7

2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃;83%
cyclohexane-diacetic acid-(1.1)-anhydride

cyclohexane-diacetic acid-(1.1)-anhydride

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With ammonia Zersetzen des Ammoniumsalzes mit 1.1 Mol 10%iger Natronlauge, Behandeln des Reaktionsprodukts mit alkal.Kaliumhypobromit-Loesung, zuletzt bei 70-75grad, und Eindampfen mit Salzsaeure;
2-(dimethylamino)-2-azaspiro[4.5]decan-3-one

2-(dimethylamino)-2-azaspiro[4.5]decan-3-one

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With magnesium monoperoxyphthalate hexahydrate In methanol at 20℃; for 3h;39 mg
1-cyclohexene-1-carboxaldehyde
1192-88-7

1-cyclohexene-1-carboxaldehyde

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: CH2Cl2 / 20 °C
2.1: DMAB; methanesulfonic acid / diethyl ether / 3 h / 0 °C
2.2: 81 percent / pyridine / CH2Cl2 / 0 °C
3.1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C
4.1: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C
View Scheme
1-cyclohexen-1-carboxaldehyde benzoylhydrazone

1-cyclohexen-1-carboxaldehyde benzoylhydrazone

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: DMAB; methanesulfonic acid / diethyl ether / 3 h / 0 °C
1.2: 81 percent / pyridine / CH2Cl2 / 0 °C
2.1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C
3.1: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C
View Scheme
N'-(1-cyclohexenylmethyl)-N'-trichloroacetylbenzohydrazide
651311-40-9

N'-(1-cyclohexenylmethyl)-N'-trichloroacetylbenzohydrazide

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C
2: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C
View Scheme
[1-Cyclohexyl-meth-(E)-ylidene]-(4-methoxy-benzyl)-amine
219915-83-0

[1-Cyclohexyl-meth-(E)-ylidene]-(4-methoxy-benzyl)-amine

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene / 1 h / 0 - 20 °C
1.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C
2.1: 26 percent / tributyltin hydride
3.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
4.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: toluene / 1 h / 0 - 20 °C
1.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C
2.1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating
3.1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating
4.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
5.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme
cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: toluene / Heating
2.1: toluene / 1 h / 0 - 20 °C
2.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C
3.1: 26 percent / tributyltin hydride
4.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
5.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: toluene / Heating
2.1: toluene / 1 h / 0 - 20 °C
2.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C
3.1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating
4.1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating
5.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
6.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme
4,4,6-trichloro-2-(dimethylamino)-2-azaspiro[4.5]decan-3-one
608532-87-2

4,4,6-trichloro-2-(dimethylamino)-2-azaspiro[4.5]decan-3-one

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Raney nickel; water / ethanol / 110 °C
2: 39 mg / magnesium monoperoxyphthalate hexahydrate / methanol / 3 h / 20 °C
View Scheme
1-hydroxy-2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one
608532-81-6

1-hydroxy-2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
2: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme
2,2,2-trichloro-N-(cyclohexylidenemethyl)-N-(4-methoxybenzyl)acetamide
608532-79-2

2,2,2-trichloro-N-(cyclohexylidenemethyl)-N-(4-methoxybenzyl)acetamide

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 26 percent / tributyltin hydride
2: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
3: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating
2: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating
3: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
4: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme
1,4,4-trichloro-2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one
608532-80-5

1,4,4-trichloro-2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating
2: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
3: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C
View Scheme
1-(aminomethyl)cyclohexaneacetic acid hydrochloride

1-(aminomethyl)cyclohexaneacetic acid hydrochloride

A

mother liquor A

mother liquor A

B

mother liquor B

mother liquor B

C

gabapentin-lactam
64744-50-9

gabapentin-lactam

D

impurity

impurity

E

H-Gpn-OH
60142-96-3

H-Gpn-OH

Conditions
ConditionsYield
With sodium hydroxide; pyrographite In water at 5 - 75℃; for 8h; Conversion of starting material;
1-(aminomethyl)cyclohexaneacetic acid hydrochloride

1-(aminomethyl)cyclohexaneacetic acid hydrochloride

A

mother liquor B

mother liquor B

B

gabapentin-lactam
64744-50-9

gabapentin-lactam

C

impurity

impurity

D

H-Gpn-OH
60142-96-3

H-Gpn-OH

Conditions
ConditionsYield
With sodium hydroxide; pyrographite In water at 0 - 70℃; for 6h; Conversion of starting material;
With sodium hydroxide; pyrographite In water at 10 - 80℃; for 11.5h; Conversion of starting material;
With sodium hydroxide; pyrographite In water at 5 - 75℃; for 11.5h; Conversion of starting material;
mother liquor A

mother liquor A

mother liquor B

mother liquor B

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
With sodium hydroxide; pyrographite In water at 80 - 85℃; for 2h;
ethyl 2-(1-formylcyclohexyl)acetate
460711-33-5

ethyl 2-(1-formylcyclohexyl)acetate

gabapentin-lactam
64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Stage #1: ethyl 2-(1-formylcyclohexyl)acetate With ammonia In ethanol at 20℃; for 48h;
Stage #2: With hydrogen; acetic acid; 5%-palladium/activated carbon at 80 - 100℃; under 2844.39 Torr; for 3h; Product distribution / selectivity;
gabapentin-lactam
64744-50-9

gabapentin-lactam

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester
898552-75-5

3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With dmap In acetonitrile at 25℃;92%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

gabapentin-lactam
64744-50-9

gabapentin-lactam

2-(3-phenylprop-1-en-1-yl)-2-azaspiro[4.5]decan-3-one

2-(3-phenylprop-1-en-1-yl)-2-azaspiro[4.5]decan-3-one

Conditions
ConditionsYield
With acetic acid In toluene at 110℃; for 12h; Dean-Stark;92%
gabapentin-lactam
64744-50-9

gabapentin-lactam

1-(aminomethyl)cyclohexaneacetic acid hydrochloride

1-(aminomethyl)cyclohexaneacetic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 80 - 90℃; for 5h; Heating / reflux;90.9%
With hydrogenchloride; water for 24h; Reflux;90%
With hydrogenchloride; water at 100℃; for 10h;90%
gabapentin-lactam
64744-50-9

gabapentin-lactam

diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

diisopropyl(3-oxo-2-azaspiro[4,5]decan-2-yl)phosphonate
1417780-49-4

diisopropyl(3-oxo-2-azaspiro[4,5]decan-2-yl)phosphonate

Conditions
ConditionsYield
With copper diacetate; potassium carbonate In toluene at 80℃; under 760.051 Torr; for 0.666667h; Reagent/catalyst; Molecular sieve;87%
gabapentin-lactam
64744-50-9

gabapentin-lactam

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-tosyl-2-azaspiro[4.5]decan-3-one

2-tosyl-2-azaspiro[4.5]decan-3-one

Conditions
ConditionsYield
Stage #1: gabapentin-lactam With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
87%
gabapentin-lactam
64744-50-9

gabapentin-lactam

benzyl alcohol
100-51-6

benzyl alcohol

2-benzoyl-2-aza-spiro[4.5]decan-3-one

2-benzoyl-2-aza-spiro[4.5]decan-3-one

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; 9-azanoradamantane N-oxyl; oxygen; copper(l) chloride In tetrahydrofuran at 23℃; for 1h; Molecular sieve;87%
gabapentin-lactam
64744-50-9

gabapentin-lactam

para-thiocresol
106-45-6

para-thiocresol

4,4-pentamethylene-N-(p-tolylthio)-2-pyrrolidone

4,4-pentamethylene-N-(p-tolylthio)-2-pyrrolidone

Conditions
ConditionsYield
With potassium fluoride; oxygen In 1,3,5-trimethyl-benzene at 100℃; under 760.051 Torr; for 1h; Autoclave;76%
gabapentin-lactam
64744-50-9

gabapentin-lactam

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

4-methyl-N-(2-azaspiro[4.5]decan-3-ylidene)benzenesulfonamide

4-methyl-N-(2-azaspiro[4.5]decan-3-ylidene)benzenesulfonamide

Conditions
ConditionsYield
With diazoacetic acid ethyl ester; manganese(II) perchlorate hexahydrate In cyclohexane at 90℃; for 12h; chemoselective reaction;72%
gabapentin-lactam
64744-50-9

gabapentin-lactam

Boc-Glu(OBzl)-OH
13574-13-5

Boc-Glu(OBzl)-OH

benzyl (S)-4-((tert-butoxycarbonyl)amino)-5-oxo-5-(3-oxo-2-azaspiro[4.5]decan-2-yl)pentanoate

benzyl (S)-4-((tert-butoxycarbonyl)amino)-5-oxo-5-(3-oxo-2-azaspiro[4.5]decan-2-yl)pentanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 5h;60%
gabapentin-lactam
64744-50-9

gabapentin-lactam

1-aminomethyl-1-cyclohexaneacetic acid hydrobromide
797762-15-3

1-aminomethyl-1-cyclohexaneacetic acid hydrobromide

Conditions
ConditionsYield
With water; hydrogen bromide at 0 - 114℃; for 6 - 24h; Product distribution / selectivity; Heating / reflux;59.27%
With water; hydrogen bromide at 0 - 114℃; for 24 - 45h; Product distribution / selectivity; Heating / reflux;59.27%
BOC-glycine
4530-20-5

BOC-glycine

gabapentin-lactam
64744-50-9

gabapentin-lactam

tert-butyl (2-oxo-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)ethyl)carbamate

tert-butyl (2-oxo-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)ethyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 5h;57%
gabapentin-lactam
64744-50-9

gabapentin-lactam

iodobenzene
591-50-4

iodobenzene

2-phenyl-2-azaspiro[4.5]decan-3-one

2-phenyl-2-azaspiro[4.5]decan-3-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; 1,3-bis(methylamino)propane In 1,4-dioxane for 24h; Reflux;50%

64744-50-9Relevant articles and documents

Synthesis of N-(2,3,4,5,6-pentafluorobenzyloxy)-γ-lactams by rhodium-catalyzed cyclization of diazo amides

Budny, Marcin,Nowak, Magdalena,Wojtczak, Andrzej,Wolan, Andrzej

, p. 6361 - 6365 (2014)

Rhodium-catalyzed cyclization of N-(2,3,4,5,6-pentafluoro-benzyloxy) diazo amides leading to the corresponding γ-lactams is described. The cyclization is based on the intramolecular catalytic insertion into the C-H bond. Fourteen lactams were obtained with up to 91 % yield and 88 % ee. Gabapentin hydrochloride, a GABA analog, was also synthesized by this method, which shows that deprotection of the 2,3,4,5,6-pentafluorobenzyloxy group is possible. The rhodium-catalyzed cyclization of diazo amides, derived from O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine, is reported. The reaction leads to a variety of lactams in up to 91 % yield and 88 % ee. The developed method was applied in the synthesis of gabapentin hydrochloride, an important GABA analog.

Rapid and Mild Lactamization Using Highly Electrophilic Triphosgene in a Microflow Reactor

Fuse, Shinichiro,Komuro, Keiji,Otake, Yuma,Masui, Hisashi,Nakamura, Hiroyuki

supporting information, p. 7525 - 7532 (2021/03/17)

Lactams are cyclic amides that are indispensable as drugs and as drug candidates. Conventional lactamization includes acid-mediated and coupling-agent-mediated approaches that suffer from narrow substrate scope, much waste, and/or high cost. Inexpensive, less-wasteful approaches mediated by highly electrophilic reagents are attractive, but there is an imminent risk of side reactions. Herein, a methods using highly electrophilic triphosgene in a microflow reactor that accomplishes rapid (0.5–10 s), mild, inexpensive, and less-wasteful lactamization are described. Methods A and B, which use N-methylmorpholine and N-methylimidazole, respectively, were developed. Various lactams and a cyclic peptide containing acid- and/or heat-labile functional groups were synthesized in good to high yields without the need for tedious purification. Undesired reactions were successfully suppressed, and the risk of handling triphosgene was minimized by the use of microflow technology.

A Simple and Expedient Procedure for the Preparation of Gabapentin Lactam (2-Aza-spiro[4,5]decan-3-one)

Katuri, Jashuva V. P.,Ekkundi, Vadiraj S.,Nagarajan, Kuppuswamy

, p. 1828 - 1832 (2016/10/31)

A novel process has been described on 100 g scale for the preparation of gabapentin lactam which is a penultimate intermediate for the preparation of gabapentin, comprising a Hofmann reaction of 1,1-cyclohexanediacetic acid monoamide using chlorinating agents such as trichloroisocyanuric acid, sodium dichloroisocyanurate, 1,3-dichloro-5,5-dimethylhydantoin, and N-chlorosuccinimide, which have not been employed so far for making this molecule. Reactions done in aqueous alkali on the 1,1-cyclohexanediacetic acid monoamide led to a solution of gabapentin sodium salt which on heating led to the formation of the gabapentin lactam in good yield.

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