(R)-(-)-5-Hydroxymethylpyrrolidin-2-one supplier

Name
5-Hydroxymethylpyrrolidin-2-one
EINECS -0
CAS No. 66673-40-3
Article Data24
CAS DataBase
Density 1.153 g/cm³
Solubility
Melting Point 83-85 °C(lit.)
Formula C₅H₉NO₂
Boiling Point 346 °C at 760 mmHg
Molecular Weight 115.132
Flash Point 163 °C
Transport Information
Appearance White powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Pyrrolidinone,5-(hydroxymethyl)-, (R)-;(-)-5-(Hydroxymethyl)-2-pyrrolidinone;(5R)-5-Hydroxymethylpyrrolidin-2-one;(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone;(R)-5-(Hydroxymethyl)pyrrolidin-2-one;(R)-5-Hydroxymethyl-2-pyrrolidinone;(R)-5-Hydroxymethyl-2-pyrrolidone;(R)-5-Hydroxymethylpyrrolidin-2-one;(R)-5-Oxopyrrolidine-2-methanol;(R)-(-)-5-hydroxymethyl-2-pyrrolidinone;
PSA 49.33000
LogP -0.41390

Synthetic route

: (R)-N-(tert-butoxycarbonyl)-5-(tert-butoxymethyl)pyrrolidin-2-one

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

Conditions

Conditions	Yield
With water; trifluoroacetic acid In dichloromethane at 50℃; for 5h;	99%

: 64700-65-8
methyl (2R)-pyroglutamate

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate at 0℃;	97%
With methanol; sodium tetrahydroborate at 0℃;	97%
With methanol; sodium tetrahydroborate at 0℃;	97%

: 68766-96-1
ethyl (R)-2-pyrrolidone-5-carboxylate

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

Conditions

Conditions	Yield
With lithium borohydride In tetrahydrofuran for 16h; Ambient temperature;	85%
With sodium tetrahydroborate In tetrahydrofuran; methanol at 5℃; for 1h;	80%
With sodium tetrahydroborate In ethanol for 2h; Ambient temperature;	79%

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / SOCl2 / 1.5 h / 80 °C 2: 85 percent / LiBH4 / tetrahydrofuran / 16 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 95 percent / thionyl chloride / 1.) 0 deg C, 30 min, 2.) room temp., 3 h 2: 78 percent / NaBH4 / ethanol / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: SOCl2 / 48 h / Ambient temperature; pH=0 2: 58 percent / NaBH4 / propan-2-ol / 20 h / Ambient temperature View Scheme

: 6893-26-1
D-Glutamic acid

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) thionyl chloride / 1a) room temp., 1 h, 1b) reflux, 30 min. 2: 32.5 g / 1.5 h / 150 °C / 15 Torr 3: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 88 percent / SOCl2, KOH / 150 °C 2: LiBH4 View Scheme
Multi-step reaction with 3 steps 1: H2O / 63 h / Heating 2: SOCl2 / 48 h / Ambient temperature; pH=0 3: 58 percent / NaBH4 / propan-2-ol / 20 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride 1.2: Amberlyst A-21 1.3: Reflux 2.1: sodium tetrahydroborate / isopropyl alcohol View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / 20 h / 20 °C 1.2: 2 h / Reflux 2.1: sodium tetrahydroborate / isopropyl alcohol / 20 h / 20 °C View Scheme

: 13107-55-6
D-glutamic acid diethyl ester

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 32.5 g / 1.5 h / 150 °C / 15 Torr 2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature View Scheme

: 13515-99-6, 23150-65-4, 27025-25-8
D-glutamic acid dimethyl ester hydrochloride

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 4 h / Reflux 2: isopropyl alcohol; sodium tetrahydroborate / 20 h / 20 °C View Scheme

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 128899-30-9, 100548-49-0, 106191-02-0
(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 4h;	100%
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	99%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 386707-15-9
methyl 3'-(cyanocarbonyl)-2,2'-binaphthalene-3-carboxylate

: C28H23NO5

Conditions

Conditions	Yield
With dmap In acetonitrile at 14℃; for 1.5h;	100%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 77-76-9
2,2-dimethoxy-propane

: (7aR)-3,3-dimethyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 1.5h; Dean-Stark; Reflux;	100%
With camphor-10-sulfonic acid at 75℃; for 20h; Reagent/catalyst; Temperature; Time; Concentration;	78%
With camphor-10-sulfonic acid at 75℃; for 20h; Time; Temperature; Reflux;	78%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 109-92-2
ethyl vinyl ether

: 67040-46-4
(5R)-5-((tert-ethoxyethoxy)methyl)pyrrolidin-2-one

Conditions

Conditions	Yield
With trichloroacetic acid In chloroform for 4h; Ambient temperature;	97%
With trichloroacetic acid In dichloromethane at 20℃; for 16h;	37%
With trichloroacetic acid In dichloromethane at 20℃; for 16h;	37%
With trichloroacetic acid In dichloromethane at 20℃; for 16h;	37%
With trichlorosilane; acetic acid In dichloromethane at 20℃; for 16h;	37%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 4042-36-8
D-pyrrolidone-5-carboxylic acid

Conditions

Conditions	Yield
With oxygen; sodium hydrogencarbonate; platinum In water for 4h; Ambient temperature;	95%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 98-59-9
p-toluenesulfonyl chloride

: 128899-31-0
<(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;	95%
With dmap; triethylamine In dichloromethane at 0 - 23℃; for 12h; Inert atmosphere;	93%
With dmap; triethylamine In dichloromethane at 20℃; for 18h; Cooling with ice;	81%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 58479-61-1
tert-butylchlorodiphenylsilane

: 138629-44-4
(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 12h; Ambient temperature;	95%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 5h;	95%
With dmap; triethylamine In dichloromethane	88%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 124-63-0
methanesulfonyl chloride

: 128811-47-2
<(2R)-5-oxopyrrolidin-2-yl>methyl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1.5h;	93%
With triethylamine In dichloromethane	85%
With triethylamine In chloroform at 0 - 20℃;	70%
With pyridine at 25℃; for 1.5h;	60%

: 925444-75-3
C17H33IOSi

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 1084897-41-5
C22H41NO3Si

Conditions

Conditions	Yield
With potassium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine In acetonitrile for 18h; Heating / reflux;	93%

: 13154-24-0
triisopropylsilyl chloride

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: (R)-5-Triisopropylsilanyloxymethyl-pyrrolidin-2-one

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	88%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 16h;	37%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 776-74-9
Bromodiphenylmethane

: (R)-5-(benzhydryloxymethyl)pyrrolidin-2-one

Conditions

Conditions	Yield
Stage #1: (R)-5-hydroxymethylpyrrolidin-2-one With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: Bromodiphenylmethane In tetrahydrofuran; mineral oil at 50℃; for 12h;	88%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 173828-76-7
(R)-5-(azidomethyl)-2-pyrrolidone

Conditions

Conditions	Yield
With hydrogen azide; di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h;	87%
With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 100-52-7
benzaldehyde

: 118918-76-6
(2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>octan-8-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark;	85%
With 4 A molecular sieve; toluene-4-sulfonic acid In toluene Heating;	72%
With toluene-4-sulfonic acid Inert atmosphere;	67%
With water; toluene-4-sulfonic acid In toluene at 20℃; Reflux;	62%
With toluene-4-sulfonic acid In toluene for 16h; Reflux;	52%

: 2362-12-1
4-Bromo-2-methylphenol

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 215382-97-1
(R)-5-(4-Bromo-2-methylphenoxymethyl)-2-pyrrolidinone

Conditions

Conditions	Yield
In ethyl acetate; SiO2	83%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 836643-56-2
[1-(4-bromo-phenyl)-hexyloxy]-tert-butyl-dimethyl-silane

: 1073241-71-0
C23H39NO3Si

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In acetonitrile Heating / reflux;	82%

: 109-87-5
Dimethoxymethane

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 1365178-37-5
C7H13NO3

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 6h; Inert atmosphere;	80%

: 5470-17-7
3-bromo-2-chloro-5-nitropyridine

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: (R)-5-(((3-bromo-5-nitropyridin-2-yl)oxy)methyl)pyrrolidin-2-one

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃; for 16h; Inert atmosphere;	79%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 98612-60-3
(5R)-5-(bromomethyl)pyrrolidin-2-one

Conditions

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane for 1.5h; Ambient temperature;	77%
With carbon tetrabromide; triphenylphosphine In acetonitrile	73%
With carbon tetrabromide; triphenylphosphine In acetonitrile at 0 - 20℃; for 24h;

: 98491-29-3
1-iodo-4-(methoxymethoxy)benzene

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: (R)-5-Hydroxymethyl-1-(4-methoxymethoxy-phenyl)-pyrrolidin-2-one

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide Heating;	71%

: 215388-44-6
3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl 2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl ketone

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 215387-32-9
3-Methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl (R)-2-[4-(5-Oxopyrrolidin-2-ylmethoxy)phenyl]benzo[b]thiophen-3-yl Ketone

Conditions

Conditions	Yield
With triethanolamine In tetrahydrofuran; SiO2	70%

: 27149-27-5
2-(4-bromophenyl)-1,3-thiazole

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 1073242-22-4
C14H14N2O2S

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In acetonitrile for 18h; Heating / reflux;	67%

: 63358-20-3
C14H29IOSi

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 1084897-20-0
C19H37NO3Si

Conditions

Conditions	Yield
With potassium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine In acetonitrile for 18h; Heating / reflux;	67%

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 138541-53-4
(R)-(+)-5-(chloromethyl)-2-pyrrolidone

Conditions

Conditions	Yield
With methanesulfonyl chloride In N,N-dimethyl-formamide at 65℃; for 16h;	65%

: 23703-22-2
1-bromo-4-n-hexylbenzene

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 1043876-44-3
C17H25NO2

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In acetonitrile for 72h; Heating/reflux;	63%
With potassium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine In acetonitrile for 72h; Reflux;	63%

: 106-43-4
para-chlorotoluene

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: (R)-5-(hydroxymethyl)-1-(p-tolyl)pyrrolidin-2-one

Conditions

Conditions	Yield
With copper(I) oxide; potassium phosphate; N1,N2-bis(thiophen-2-ylmethyl)oxalamide In tert-butyl alcohol at 130℃; for 24h; Schlenk technique;	58%

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

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 58479-61-1
tert-butylchlorodiphenylsilane

: 149-73-5
trimethyl orthoformate

: 203301-82-0
(5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine

Conditions

Conditions	Yield
Multistep reaction.;	52%

...Expand

: 193966-79-9
6-benzyloxy-2-(4-hydroxyphenyl)-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophene

: 66673-40-3
(R)-5-hydroxymethylpyrrolidin-2-one

: 215388-70-8
(R)-6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-(5-oxopyrrolidin-2-ylmethoxy)phenyl]benzo[b]thiophene

Conditions

Conditions	Yield
	50%

(R)-(-)-5-Hydroxymethylpyrrolidin-2-one Chemical Properties

IUPAC Name: (5R)-5-(hydroxymethyl)pyrrolidin-2-one
Synonyms: (R)-5-HYDROXYMETHYL-PYRROLIDIN-2-ONE;(R)-(-)-5-(HYDROXYMETHYL)-2-PYRROLIDINONE;(R)-5-(HYDROXYMETHYL)-2-PYRROLIDINONE; D-PYROGLUTAMINOL;(-)-D-PYROGLUTAMOL;(R)-(-)-5-(HYDROXYMETHYL)-2-PYRROLIDONE;(R)-(-)-2-PYRROLIDONE-5-YL-METHANOL;
The Molecular formula of 5-Hydroxymethylpyrrolidin-2-one(66673-40-3): C₅H₉NO₂
The Molecular Weight of 5-Hydroxymethylpyrrolidin-2-one(66673-40-3): 115.13
Molecular Structure :

Surface Tension: 38.7 dyne/cm
Density: 1.153 g/cm³
Flash Point: 163 °C
Enthalpy of Vaporization: 68.34 kJ/mol
Boiling Point: 346 °C at 760 mmHg
Vapour Pressure: 3.72E-06 mmHg at 25°C
Appearance: White Powder

(R)-(-)-5-Hydroxymethylpyrrolidin-2-one Safety Profile

The Hazard Codes of 5-Hydroxymethylpyrrolidin-2-one(66673-40-3):

Xi
The Risk Statements information of 5-Hydroxymethylpyrrolidin-2-one(66673-40-3):
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements information of 5-Hydroxymethylpyrrolidin-2-one(66673-40-3):
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany: 3
F: 3-10

Product Name

5-Hydroxymethylpyrrolidin-2-one

Synthetic route

(R)-(-)-5-Hydroxymethylpyrrolidin-2-one Chemical Properties

(R)-(-)-5-Hydroxymethylpyrrolidin-2-one Safety Profile

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