(3R)-(+)-3-(ETHYLAMINO)PYRROLIDINE synthesis
- Product Name:(3R)-(+)-3-(ETHYLAMINO)PYRROLIDINE
- CAS Number:381670-30-0
- Molecular formula:C6H14N2
- Molecular Weight:114.19
115445-21-1
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381670-30-0
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Yield:381670-30-0 61%
Reaction Conditions:
with ammonium formate;palladium hydroxide on carbon in methanol; for 2.5 h;Heating / reflux;
Steps:
I.12
To a mechanically stirred solution of (3R)-N-ethyl-1-(phenylmethyl)-3-pyrrolidinamine (140 g, 686 mmol) in methanol (1.2 L) was added palladium hydroxide on carbon (18 g, 25.6 mmol) and ammonium formate (173 g, 2743 mmol). The reaction was heated at reflux for 2.5 hrs. After cooling to RT, the reaction was filtered and the filtrate was concentrated. The oil was taken up in THF (80OmL) and cooled in an ice bath. 50% aqueous sodium hydroxide (71 mL) was added, and the mixture was stirred for 15 minutes. Magnesium sulfate (35 g) was added, and the mixture was stirred for 15 minutes. The mixture was diluted with DCM (1 L), and filtered through Celite. The filtrate was concentrated, taken up in fresh DCM, dried over magnesium sulfate, and concentrated to afford the desired crude product as a yellow oil (47.8 g, 61 %): 1H NMR (400 MHz, CDCI3) δ ppm 3.19 - 3.28 (m, 1 H), 3.04 (ddd, J = 10.97, 7.99, 6.1 1 Hz, 1 H), 2.95 (dd, J = 1 1.41 , 6.06 Hz, 1 H),2.80 - 2.89 (m, 1 H), 2.72 (dd, J = 11.36, 4.06 Hz, 1 H), 2.52 - 2.65 (m, 3 H), 1 .95 (td, J = 13.36, 7.61 Hz, 1 H), 1.43 - 1.54 (m, 1 H), 1.07 (t, J = 7.09 Hz, 3 H).
References:
WO2009/76387,2009,A1 Location in patent:Page/Page column 24