(-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

Base Information

• Chemical Name: (-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one
• CAS No.: 1273550-98-3
• Molecular Formula: C₁₆H₁₉NO₄
• Molecular Weight: 289.331

Synonyms:(-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

Chemical Property of (-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

Chemical Property:

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Technology Process of (-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one

There total 3 articles about (-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1S,9aS)-1-benzoyloxy-9-diphenyl(methyl)silyloxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one → (-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one (1273550-98-3) + <1S-(1β,9β,9a-β)>-1-(Benzoyloxy)octahydro-9-hydroxy-4H-quinolizin-4-one (155768-67-5)

Guidance literature:

With water; toluene-4-sulfonic acid; In methanol; at 20 ℃; for 1h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tet.2010.12.048

Reference yield:

C16H17NO4 → (-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one (1273550-98-3)

Guidance literature:

With L-Selectride; In tetrahydrofuran; for 0.666667h; Inert atmosphere; Cooling with acetone-dry ice;

DOI:10.1016/j.tet.2010.12.048

Reference yield:

(1S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one → (-)-(1S,9S,9aR)-1-benzoyloxy-9-hydroxy-1,2,3,6,7,8,9,9a-octahydro-4H-quinolizin-4-one (1273550-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

2: L-Selectride / tetrahydrofuran / 0.67 h / Inert atmosphere; Cooling with acetone-dry ice

With L-Selectride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2010.12.048

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