| Identification | Back Directory | [Name]
(S)-5-(BROMOMETHYL)-2-PYRROLIDINONE | [CAS]
72479-05-1 | [Synonyms]
(S)-5-(BromomethyL
(S)-5-(BROMOMETHYL)-2-PYRROLIDONE
5β-(Bromomethyl)pyrrolidine-2-one
(S)-5-BROMOMETHYL-2-OXOPYRROLIDINE
(S)-5-(BROMOMETHYL)-2-PYRROLIDINONE
(S)-5-(broMoMethyl)pyrrolidin-2-one
(5S)-5-(bromomethyl)-2-pyrrolidinone
(5S)-5-(broMoMethyl)pyrrolidin-2-one
(5S)-5β-(Bromomethyl)pyrrolidine-2-one
2-Pyrrolidinone, 5-(bromomethyl)-, (5S)-
[S,(-)]-5β-(Bromomethyl)pyrrolidine-2-one
2-Pyrrolidinone,5-(bromomethyl)-,(5S)-(9CI) | [Molecular Formula]
C5H8BrNO | [MDL Number]
MFCD01632456 | [MOL File]
72479-05-1.mol | [Molecular Weight]
178.03 |
| Chemical Properties | Back Directory | [Melting point ]
75-79°C | [Boiling point ]
102-106 °C(Press: 0.1 Torr) | [density ]
1.541±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
powder | [pka]
15.39±0.40(Predicted) | [Appearance]
Off-white to light brown Solid | [Optical Rotation]
[α]22/D 30.0°, c = 0.5 in ethanol |
| Hazard Information | Back Directory | [Chemical Properties]
White to tan powder | [Synthesis]
General procedure for the synthesis of (S)-5-bromomethyl-2-pyrrolidinone from (S)-(+)-5-hydroxymethyl-2-pyrrolidinone: First, (S)-5-hydroxymethyl-2-pyrrolidinone (1.58 g, 13.7 mmol) and triphenylphosphine (3.97 g, 15.1 mmol) were suspended in anhydrous acetonitrile (20 mL) and stirred at 0 °C. Subsequently, a solution of carbon tetrabromide (5.02 g, 15.1 mmol, 1.1 eq.) dissolved in 8 mL of anhydrous acetonitrile was added slowly and dropwise. The reaction mixture gradually changed to a clarified solution, followed by stirring at room temperature overnight. Upon completion of the reaction, the solvent was removed by rotary evaporation and the residue was purified by Biotage fast chromatography to afford the target product (S)-5-bromomethyl-2-pyrrolidinone as a white solid (2.32 g, 95% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CD3OD): δ 6.18 (br s, 1H), 3.94-3.97 (m, 1H), 3.28-3.44 (m, 2H), 2.27-2.49 (m, 3H), 1.82-1.91 (m, 1H). | [References]
[1] Helvetica Chimica Acta, 1996, vol. 79, # 4, p. 961 - 972
[2] Patent: WO2012/21712, 2012, A1. Location in patent: Page/Page column 162
[3] Journal of Organic Chemistry, 1980, vol. 45, # 5, p. 815 - 818
[4] Journal of the American Chemical Society, 1990, vol. 112, # 2, p. 838 - 845
[5] Tetrahedron, 2013, vol. 69, # 27-28, p. 5647 - 5659 |
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