Chemical Properties
(R)-5-(Hydroxymethyl)-2-pyrrolidinone is White Powder
Uses
(R)-5-(Hydroxymethyl)-2-pyrrolidinone is a 2-pyrrolidone derivative for therapeutic use as prostanoid receptor agonist.
Uses
Serves as a building block in the synthesis of diphthamide.
Synthesis
Scheme 1, Step B: Preparation of (R)-(-)-5-(hydroxymethyl)-2-pyrrolidinone (3)
To a solution of methanol (100 mL) containing methyl (R)-5-oxopyrrolidine-2-carboxylate (Intermediate 2, 13.2 g), sodium borohydride (10.5 g, 278 mmol) was added in batches at 0 °C. The reaction mixture was stirred continuously at 0 °C until the reaction was complete, followed by the addition of acetic acid (3 mL) to quench the reaction. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography using methanol-chloroform (1:9, v/v) as eluent to afford the target product (12.9 g, 97% yield) as a colorless solid. Thin-layer chromatography (TLC) showed an Rf value of 0.33 (unfolding agent system: methanol-chloroform, 1:9, v/v); nuclear magnetic resonance hydrogen spectrum (1H-NMR, CDCl3) δ: 7.17 (s, 1H), 3.92 (s, 1H), 3.85-3.75 (m, 1H), 3.64-3.40 (m, 2H), 2.42-2.35 (m. 2H), 2.2-2.05 (m, 1H), 1.88-1.7 (m, 1H).
References
[1] Patent: WO2014/15246, 2014, A1. Location in patent: Paragraph 0447-0448
[2] Patent: WO2014/144610, 2014, A1. Location in patent: Paragraph 0368; 0377; 0378
[3] Patent: WO2015/9991, 2015, A2. Location in patent: Paragraph 0555-0556
[4] Patent: US2016/60216, 2016, A1. Location in patent: Paragraph 0371-0372
[5] Patent: KR2015/130326, 2015, A. Location in patent: Page/Page column 0409-0411
