| Identification | Back Directory | [Name]
3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI) | [CAS]
100189-16-0 | [Synonyms]
5-(1-Hydroxyethyl)
α,6-DiMethyl-3-pyridineMethanol
1-(6-Methyl-3-pyridinyl)ethanol
a,6-diMethyl-3-PyridineMethanol
3-Pyridinemethanol, a,6-dimethyl-
3-Pyridinemethanol, α,6-dimethyl-
5-(1-Hydroxyethyl)-2-methylpyridine
3-(1-Hydroxyethyl)-6-Methylpyridine
dl-2-Methyl-5-[1-hydroxyethyl]pyridine
3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI) | [EINECS(EC#)]
125-856-9 | [Molecular Formula]
C8H11NO | [MDL Number]
MFCD06637422 | [MOL File]
100189-16-0.mol | [Molecular Weight]
137.18 |
| Chemical Properties | Back Directory | [Boiling point ]
135 °C(Press: 10 Torr) | [density ]
1.055±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [pka]
13.77±0.20(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Uses]
5-(1-Hydroxyethyl)-2-methylpyridine is an intermediate used in the synthesis of metabolites of the antidiabetic, antihyperglycemic agent Pioglitazone (P471000).
| [Synthesis]
General procedure for the synthesis of 6-methyl-3-(1-hydroxyethyl)pyridine from 1-(6-methylpyridin-3-yl)ethanone: Sodium borohydride (2.3 g, 0.06 mol) was added in batches to a solution of 1-(6-methylpyridin-3-yl)ethanol (160 ml) of 1-(6-methylpyridin-3-yl)ethanone (16.4 g, 0.121 mol) at 30 °C, maintaining a constant temperature and continuously stirring the reaction mixture. After 1 hour of reaction, the reaction mixture was diluted with saturated sodium bicarbonate solution (2 x 200 ml) and subsequently extracted with dichloromethane (2 x 500 ml). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give a light yellow oil. The crude product was purified by fast column chromatography (eluent: 5% methanol/dichloromethane) to afford 6-methyl-3-(1-hydroxyethyl)pyridine (17.0 g, two-step yield 93%) as a pale yellow oil.ES-MS [M + 1]+ : 138.1. 1H NMR (400 MHz, CDCl3): δ 8.35 (d, J = 2.0 Hz, 1H), δ 7.63 (dd, J = 8.0,2.4 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 4.89 (q, J = 6.5 Hz, 1H), 3.30 (brs, 1H), 2.50 (s, 3H), 1.48 (d, J = 6.5 Hz, 3H). | [References]
[1] Journal of Medicinal Chemistry, 1996, vol. 39, # 26, p. 5053 - 5063
[2] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 12, p. 2168 - 2172
[3] Chemische Berichte, 1947, vol. 80, p. 502,505
[4] Patent: WO2009/80637, 2009, A1. Location in patent: Page/Page column 32
[5] Patent: WO2015/150476, 2015, A1. Location in patent: Page/Page column 23; 24 |
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