(5-methylpyrrolidin-3-yl)methanol synthesis
- Product Name:(5-methylpyrrolidin-3-yl)methanol
- CAS Number:937665-89-9
- Molecular formula:C6H13NO
- Molecular Weight:115.17
1224433-86-6
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937665-89-9
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Yield:937665-89-9 100%
Reaction Conditions:
with 20% palladium hydroxide-activated charcoal;hydrogen in ethanol at 20; under 757.576 Torr; for 16.25 h;Inert atmosphere;
Steps:
12.D j231j Part D. Preparation of (5-methylpyrrolidin-3-yl)methanol.
A solution of (1-benzyl-5-methylpyrrolidin-3-yl)methanol (5.53 g, 26.9 mmol) in ethanol(192 mL) was put under vacuum and backfilled with nitrogen three times. Palladiumhydroxide on carbon (20 wt. %, 50% wet) (1.89 g) was added. Hydrogen was bubbled intothe suspension 0.25 hr. The resulting mixture was stirred under 1.01 bar of hydrogen 16hr at room temperature. The mixture was then filtered on a pad of diatomaceous earth. The filter cake was washed with ethanol and the filtrate was concentrated under reduced pressure to provide (5-methylpyrrolidin-3-yl)methanol (3.16 g, quant., mixture of diastereoisomers) as an oil. ‘H NMR (300 MHz, CDC13): ppm 0.96 - 1.06 (m, 0.5 H),1.14 and 1.18 (2 d, J= 6.35 and 6.19 Hz, 3 H), 1.37- 1.47 (m, 0.5 H), 1.65 - 1.74 (m, 0.5 H), 2.00 - 2.15 (m, 3 H), 2.27 -2.43 (m, 1 H), 2.63 (dd, J= 10.90, 6.50 Hz, 0.5 H), 2.86 - 3.00(m, 1 H), 3.06-3.24(m, 1 H), 3.48-3.66(m,2H).
References:
WO2014/117274,2014,A1 Location in patent:Paragraph 231
108-27-0
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