ChemicalBook--->CAS DataBase List--->17342-08-4

17342-08-4

17342-08-4 Structure

17342-08-4 Structure
IdentificationMore
[Name]

L-Pyroglutaminol
[CAS]

17342-08-4
[Synonyms]

H-PGLU-OL
H-PYR-OL
L-PYROGLUTAMINOL
(+)-L-PYROGLUTAMOL
PGLU-OL
PYROGLUTAMINOL
(S)-(+)-5-(HYDROXYMETHYL)-2-PYRROLIDINONE
(S)-5-(HYDROXYMETHYL)-2-PYRROLIDINONE
TIMTEC-BB SBB004302
(S)-5-Hydroxymethyl-Pyrrolidin-2-One
(S)-(+)-5-HYDROXYMETHYL-2-PYRROLIDINONE 97%
(S)-5-Hydroxy-2-pyrrolidine
[EINECS(EC#)]

605-678-7
[Molecular Formula]

C5H9NO2
[MDL Number]

MFCD00077792
[Molecular Weight]

115.13
[MOL File]

17342-08-4.mol
Chemical PropertiesBack Directory
[Appearance]

white to light yellow crystals or
[Melting point ]

79-80 °C(lit.)
[alpha ]

30 º (C=2, ETOH)
[Boiling point ]

147-149°C 0,06mm
[density ]

1.1808 (rough estimate)
[refractive index ]

31 ° (C=5, EtOH)
[Fp ]

147-149°C/0.06m
[storage temp. ]

Store at 0-5°C
[solubility ]

DMSO, Ethanol, Methanol
[form ]

Crystals or Crystalline Powder
[pka]

14.35±0.10(Predicted)
[color ]

White to light yellow
[Optical Rotation]

[α]20/D +30°, c = 2 in ethanol
[Water Solubility ]

Soluble in water.
[BRN ]

4657914
[InChI]

1S/C5H9NO2/c7-3-4-1-2-5(8)6-4/h4,7H,1-3H2,(H,6,8)/t4-/m0/s1
[InChIKey]

HOBJEFOCIRXQKH-BYPYZUCNSA-N
[SMILES]

OC[C@@H]1CCC(=O)N1
[CAS DataBase Reference]

17342-08-4(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264-P271-P280-P302+P352-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[F ]

3-10
[HS Code ]

29051990
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium hydroxide-->Ethyl acetate-->Methanol-->Dichloromethane-->Acetic acid-->Thionyl chloride-->Acetone-->Sodium bicarbonate-->Sodium borohydride-->Isopropyl alcohol-->L-Glutamic acid
[Preparation Products]

2-PyrrolidineMethanol, 4-hydroxy-, hydrochloride (1:1), (2S,4R)--->(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate-->(+)-(3R,7aS)-Tetrahydro-3-phenyl-3H,5H-pyrrolo1,2-coxaole-5-one-->L-(+)-Glutamic acid hydrochloride-->(S)-5-(fluoromethyl)pyrrolidin-2-one
Hazard InformationBack Directory
[Chemical Properties]

white to light yellow crystals or
[Uses]

(S)-Pyroglutaminol (cas# 17342-08-4) is a compound useful in organic synthesis.
[Synthesis]

Ethyl L-pyroglutamate

7149-65-7

L-Pyroglutaminol

17342-08-4

General procedure for the synthesis of (S)-(+)-5-hydroxymethyl-2-pyrrolidinone from ethyl (S)-5-oxopyrrolidine-2-carboxylate: compound III was synthesized as follows: firstly, LiCl (18 mmol) was added to the reaction flask and dissolved in anhydrous tetrahydrofuran (15 ml). The temperature of the reaction system was controlled at -15 to -10°C. Subsequently, potassium borohydride (18 mmol) was added to the system and the reaction was stirred for 30 minutes. In another reaction flask, compound II (9 mmol) was dissolved in anhydrous tetrahydrofuran (20 ml) and cooled to -15 to -10 °C. Then, the previously prepared reaction solution was slowly added dropwise to this system. After the dropwise addition, the reaction was slowly warmed up to room temperature for 2 hours. The reaction process was monitored by TLC to confirm the complete reaction of the raw materials. Next, saturated ammonium chloride solution (5 ml) was added slowly dropwise to the reaction system and stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate, the organic phases were combined and dried with anhydrous sodium sulfate. The dried organic phase was filtered and the filtrate was concentrated under reduced pressure to give compound III (8.55 mmol) in 95% yield.

[References]

[1] Patent: CN107304179, 2017, A. Location in patent: Paragraph 0033; 0036-0037; 0055; 0058;
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 4, p. 437 - 445
[3] Tetrahedron, 1996, vol. 52, # 10, p. 3719 - 3740
[4] Patent: WO2015/181676, 2015, A1. Location in patent: Page/Page column 170-171
[5] Journal of Organic Chemistry, 1992, vol. 57, # 7, p. 2158 - 2160
Spectrum DetailBack Directory
[Spectrum Detail]

L-Pyroglutaminol(17342-08-4)1HNMR
L-Pyroglutaminol(17342-08-4)Raman
L-Pyroglutaminol(17342-08-4)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

(S)-(+)-5-Hydroxymethyl-2-pyrrolidinone, 97%(17342-08-4)
[Alfa Aesar]

(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone, 98%(17342-08-4)
[Sigma Aldrich]

17342-08-4(sigmaaldrich)
[TCI AMERICA]

(S)-5-(Hydroxymethyl)-2-pyrrolidinone,>98.0%(GC)(17342-08-4)
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