(2'S,3S)-1-(2-METHYLAMINO-2-PHENYL-ETHYL)-PYRROLIDIN-3-OL synthesis
- Product Name:(2'S,3S)-1-(2-METHYLAMINO-2-PHENYL-ETHYL)-PYRROLIDIN-3-OL
- CAS Number:142773-73-7
- Molecular formula:C13H20N2O
- Molecular Weight:220.31
![Carbamic acid, N-?[(1S)?-?2-?[(3S)?-?3-?hydroxy-?1-?pyrrolidinyl]?-?2-?oxo-?1-?phenylethyl]?-?, ethyl ester](/CAS/20210111/GIF/207847-98-1.gif)
207847-98-1
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Yield:142773-73-7 90%
Reaction Conditions:
with lithium aluminium tetrahydride in tetrahydrofuran at 0; for 3 h;Reflux;
Steps:
9.iii Step-ui: Synthesis of (S)- I -((S)-2-(methylamino)-2-phenylethyl)pyffolidin-3-ol
LAH (0.78g. 20.5rnmol) was dissolved in dry THF (10m1) at 0-5°C, followed by addition of ((S)-2-((S)-3 -hydroxypyrrolidin- 1 -yl)-2-oxo- 1 -phenylethyl) (1 . 5g,5.l3mmol) in THF (lOmi). The reaction mixture was refluxed for 3h, quenched with saturated Na2CO3 solution and triturated with ethyl acetate. The reaction mixture was filtered through celite and organic layer was concentrated under reduce pressure to get the (S)-1-((S)-2-(methylamino)-2-phenylethyl)pyrroliclin-3-ol, as a pale yellow oil. (1.02, 90% yield).‘H NMR: (DMSO-d6, 400 MHz): 7.37-7.27 (m, 4H), 7.26-7.23 (m, 1H), 4.80-4.68 (m, IH), 4.27-4.16 (m, 1H), 3.69-3.62 (m, 2H), 2.78-2.62 (m, 2H), 2.52 (s, 3H), 2.25-2.12 (m, 2H), 1.77-1.64 (m, 2H); ESI-MS: (+ve mode) 221.05 (M+H) (100 %).
References:
WO2015/114660,2015,A1 Location in patent:Page/Page column 25
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