(R)-(+)-4-hydroxy-2-pyrrolidinone supplier

Name
2-Pyrrolidinone,4-hydroxy-, (4R)-
EINECS
CAS No. 22677-21-0
Article Data23
CAS DataBase
Density 1.292 g/cm³
Solubility Slightly soluble in water.
Melting Point 156-160 °C
Formula C₄H₇NO₂
Boiling Point 363.6 °C at 760 mmHg
Molecular Weight 101.105
Flash Point 173.7 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Pyrrolidinone,4-hydroxy-, (R)- (8CI);(4R)-4-Hydroxy-2-pyrrolidinone;(4R)-4-Hydroxypyrrolidin-2-one;(R)-4-Hydroxy-2-pyrrolidinone;(R)-4-Hydroxypyrrolidin-2-one;
PSA 49.33000
LogP -0.80400

Synthetic route

: 10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4
ethyl (L)-4-chloro-3-hydroxybutyrate

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

Conditions

Conditions	Yield
With ammonium hydroxide at 80℃; for 3h;	82%

: 135056-42-7
1-(1'-phenylethyl)-4-phenylmethoxypyrrolidin-2-one

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

Conditions

Conditions	Yield
With ammonia; sodium In tetrahydrofuran for 1h;	51%

: 131653-48-0
(4R)-4-hydroxy-1-<(1S)-1-phenylethyl>pyrrolidin-2-one

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

Conditions

Conditions	Yield
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -60℃; for 0.25h;

: (R)-4-Hydroxy-4,5-dihydro-3H-pyrrole-2-carboxylic acid anion

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide at 40℃; for 0.75h; Yield given;

: ethyl (R)-4-amino-3-hydroxybutanoate hydrochloride

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 208103-39-3
3(R)-hydroxy-4-aminobutyric acid ethyl ester

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

Conditions

Conditions	Yield
In ethanol

Ru2Cl4((S)-BINAP)2·NEt3in: Ru2Cl4((S)-BINAP)2·NEt3in

: ammonium salt of methyl 4-amino-3-oxobutanoate

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

Conditions

Conditions	Yield
In methanol

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 18162-48-6
tert-butyldimethylsilyl chloride

: 131653-51-5
(4R)-4-((tert-butyl(dimethyl)silyl)oxy)pyrrolidin-2-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Condensation;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	95%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h;	91%

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 58479-61-1
tert-butylchlorodiphenylsilane

: 945635-00-7
(R)-4-[tert-butyl(diphenyl)silanyloxy]pyrrolidin-2-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 0.5h;	96%

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 7013-07-2
(R)-4-Amino-3-hydroxybutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride for 4h; Heating;	94%
With lithium hydroxide for 24h; Ambient temperature;	89%
With hydrogenchloride for 2h; Heating;	70%
With barium dihydroxide
With hydrogenchloride for 10h; Heating; Yield given;

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 13154-24-0
triisopropylsilyl chloride

: C13H27NO2Si

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; Cooling with ice;	81%

: 852333-59-6
4-(4,6-dichloropyridin-2-yl)morpholine

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: (4R)-1-[4-chloro-6-(morpholin-4-yl)pyridin-2-yl]-4-hydroxypyrrolidin-2-one

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	78%

: 143-07-7
lauric acid

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: (R)-4-lauroyloxy-2-pyrrolidinone

Conditions

Conditions	Yield
With pyridine; dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	60%

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 1362910-89-1
7-bromo-2-(difluoro(4-fluorophenyl)methyl)-4-(methylthio)quinazoline

: 1362910-95-9
(R)-1-(2-(difluoro(4-fluorophenyl)methyl)-4-(methylthio)quinazolin-7-yl)-4-hydroxypyrrolidin-2-one

Conditions

Conditions	Yield
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; Inert atmosphere;	48%

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 7-chloro-1-(2,4-difluorophenyl)-4-oxo-N-[(2S)-1,1,1-trifluorobutan-2-yl]-1,4-dihydro-1,8-naphthyridine-3-carboxamide

: 1-(2,4-difluorophenyl)-7-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]-4-oxo-N-[(2S)-1,1,1-trifluorobutan-2-yl]-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; Inert atmosphere;	39%

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 202865-85-8
1-bromo-4-iodo-2-methylbenzene

: 1253926-33-8
(R)-1-(4-bromo-3-methyl-phenyl)-4-hydroxy-pyrrolidin-2-one

Conditions

Conditions	Yield
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; Inert atmosphere;	38%

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 899806-32-7
(S)-4-azidopyrrolidin-2-one

Conditions

Conditions	Yield
Stage #1: (R)-4-hydroxy-2-pyrrolidinone With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 1h; Stage #2: With sodium azide In N,N-dimethyl-formamide at 60℃; for 3h;	32%

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 104-83-6
1-Chloro-4-(chloromethyl)benzene

: (R)-4-[(4-chlorobenzyl)oxy]-2-pyrrolidinone

Conditions

Conditions	Yield
Stage #1: (R)-4-hydroxy-2-pyrrolidinone With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 1-Chloro-4-(chloromethyl)benzene In N,N-dimethyl-formamide at 20℃;	30%

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 105-36-2
ethyl bromoacetate

: 68252-27-7
ethyl (R)-4-hydroxy-2-oxo-1-pyrrolidineacetate

Conditions

Conditions	Yield
With sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane 1) reflux, 2 h; 2) acetonitrile, reflux, 30 min; Multistep reaction;

: 67-56-1
methanol

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: (R)-4-Hydroxy-5-methoxy-pyrrolidin-2-one

Conditions

Conditions	Yield
With sodium phenylsulfonate at 15℃; Product distribution; Further Variations:; Reagents; electrode material; current density; Oxidation; methoxylation; Electrochemical reaction;
With sodium phenylsulfonate at 15℃; Oxidation; methoxylation; Electrochemical reaction;
With sodium phenylsulfonate at 20℃; Etherification; Electrolysis;

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

t-BuMe2SiX: t-BuMe2SiX

: 131653-51-5
(4R)-4-((tert-butyl(dimethyl)silyl)oxy)pyrrolidin-2-one

Conditions

Conditions	Yield
Substitution;

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 914103-95-0
[2-(4-(bromomethyl)phenyl)ethyl]carbamic acid tert-butyl ester

: 914104-03-3
tert-butyl [2-(4-{[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]methyl}phenyl)ethyl]carbamate

Conditions

Conditions	Yield
Stage #1: (R)-4-hydroxy-2-pyrrolidinone; [2-(4-(bromomethyl)phenyl)ethyl]carbamic acid tert-butyl ester With sodium hydride In N,N-dimethyl-formamide at 1 - 30℃; for 1h; Stage #2: With potassium hydrogensulfate; water In ethyl acetate; N,N-dimethyl-formamide

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 507-09-5
thioacetic acid

: 1972-28-7
diethylazodicarboxylate

: (4S)-4-acetylthio-2-pyrrolidone

Conditions

Conditions	Yield
With triphenylphosphine In tetrahydrofuran
With triphenylphosphine In tetrahydrofuran

...Expand

: 212267-75-9
6-bromo-N-[(2,6-dimethylphenyl)methyl]-2,3-dimethylimidazo[1,2-a]pyridin-8-amine

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: (4R)-1-(8-{[(2,6-dimethylphenyl)methyl]amino}-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-4-hydroxy-2-pyrrolidinone

Conditions

Conditions	Yield
With potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide In 1,4-dioxane at 140℃; for 14h; Ullmann-type coupling; Microwave synthesizer;

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 74-88-4
methyl iodide

: 787636-39-9
4-methoxy-1-methylpyrrolidin-2-one

Conditions

Conditions	Yield
Stage #1: (R)-4-hydroxy-2-pyrrolidinone With sodium hydride In tetrahydrofuran at 20 - 50℃; for 22h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 70h;

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 1422497-68-4
4-(4-bromo-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

: 1422500-11-5
(4R)-1-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-4-hydroxypyrrolidin-2-one

Conditions

Conditions	Yield
With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; potassium carbonate In diethylene glycol dimethyl ether at 140℃; for 2h; Microwave irradiation;	160 mg

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 98-59-9
p-toluenesulfonyl chloride

: C11H13NO4S

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 16h;

: 22677-21-0
(R)-4-hydroxy-2-pyrrolidinone

: 24424-99-5
di-tert-butyl dicarbonate

: 18162-48-6
tert-butyldimethylsilyl chloride

: C15H31NO4Si

Conditions

Conditions	Yield
Stage #1: (R)-4-hydroxy-2-pyrrolidinone; di-tert-butyl dicarbonate Stage #2: tert-butyldimethylsilyl chloride With lithium triethylborohydride

...Expand

(R)-(+)-4-hydroxy-2-pyrrolidinone Chemical Properties

IUPAC Name: (4R)-4-Hydroxypyrrolidin-2-one
Synonyms of (R)-(+)-4-hydroxy-2-pyrrolidinone (CAS NO.22677-21-0): (R)-4-Hydroxy-2-pyrrolidinone ; (R)-Beta-Hydroxy-gamma-butyrolactam ; 2-Pyrrolidinone, 4-hydroxy-, (R) ; (R)-4-Hydoroxyoyrolidone ; 4-Hydroxy-R-2-pyrrolidine
CAS NO: 22677-21-0
Molecular Formula: C₄H₇NO₂
Molecular Weight: 101.1
Molecular Structure:
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 29.54Å²
Index of Refraction: 1.513
Molar Refractivity: 23.51 cm³
Molar Volume: 78.2 cm³
Surface Tension: 50.8 dyne/cm
Density: 1.292 g/cm³
Flash Point: 173.7 °C
Enthalpy of Vaporization: 70.57 kJ/mol
Boiling Point: 363.6 °C at 760 mmHg
Vapour Pressure: 9.26E-07 mmHg at 25°C
Melting Point: 156-160 °C
Appearance: white to light yellow crystal powder
SMILES: O=C1NC[C@H](O)C1
InChI: InChI=1/C4H7NO2/c6-3-1-4(7)5-2-3/h3,6H,1-2H2,(H,5,7)/t3-/m1/s1
InChIKey: IOGISYQVOGVIEU-GSVOUGTGBE
Std. InChI: InChI=1S/C4H7NO2/c6-3-1-4(7)5-2-3/h3,6H,1-2H2,(H,5,7)/t3-/m1/s1
Std. InChIKey: IOGISYQVOGVIEU-GSVOUGTGSA-N
Product Categories of (R)-(+)-4-hydroxy-2-pyrrolidinone (CAS NO.22677-21-0): Drug Intermediates;Pyrrole&Pyrrolidine&Pyrroline

(R)-(+)-4-hydroxy-2-pyrrolidinone Safety Profile

Safety Information of (R)-(+)-4-hydroxy-2-pyrrolidinone (CAS NO.22677-21-0):
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3

Product Name

2-Pyrrolidinone,4-hydroxy-, (4R)-

Synthetic route

(R)-(+)-4-hydroxy-2-pyrrolidinone Chemical Properties

(R)-(+)-4-hydroxy-2-pyrrolidinone Safety Profile

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