Ethanone, 1-[(2S)-2,3-dihydro-2-(hydroxyMethyl)-1H-indol-1-yl]- synthesis

6synthesis methods

Product Name:Ethanone, 1-[(2S)-2,3-dihydro-2-(hydroxyMethyl)-1H-indol-1-yl]-
CAS Number:297765-25-4
Molecular formula:C11H13NO2
Molecular Weight:191.23

16851-56-2
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Ethanone, 1-[(2S)-2,3-dihydro-2-(hydroxyMethyl)-1H-indol-1-yl]-

297765-25-4
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Yield:-

Steps:

Multi-step reaction with 5 steps
1: 91 percent / thionyl chloride / 0 - 20 °C
2: 89 percent / triethylamine; 4-(dimethylamino)pyridine / tetrahydrofuran / 20 - 40 °C
3: 85 percent / DDQ / toluene / 24 h / Heating
4: chiral ferrocene-based complex; triethylamine; hydrogen / [Rh(nbd)2]SbF₆ / propan-2-ol / 0.5 h / 100 °C / 76000 Torr
5: 74 percent / lithium borohydride / tetrahydrofuran / 5 h / 20 °C

References:

Kuwano, Ryoichi;Kashiwabara, Manabu;Sato, Koji;Ito, Takashi;Kaneda, Kohei;Ito, Yoshihiko [Tetrahedron Asymmetry,2006,vol. 17,# 4,p. 521 - 535]

110592-39-7 Synthesis