(3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole

Base Information

• Chemical Name: (3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole
• CAS No.: 1374399-79-7
• Molecular Formula: C₂₉H₂₈N₂O₂
• Molecular Weight: 436.554
• Mol file: 1374399-79-7.mol

Synonyms:(3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole

Chemical Property of (3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole

There total 1 articles about (3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole 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: 66.0%

1-benzyl-2-butanoyl-3-indoleacetic acid (1374399-77-5) + D-2-phenylglycinol (56613-80-0) → (3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole (1374399-79-7)

Guidance literature:

In benzene; for 18h; Reflux;

DOI:10.1002/ejoc.201101718

Reference yield: 70.0%

(3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole (1374399-79-7) → (R)-9-benzyl-2-[(R)-2-hydroxy-1-phenylethyl]-1-propyl-1,2,3,4-tetrahydropyrido[3,4-b]indole (1374399-80-0)

Guidance literature:

With aluminum (III) chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at -33 - 20 ℃; for 4h; stereoselective reaction;

DOI:10.1002/ejoc.201101718

Reference yield:

(3R,11bS)-11-benzyl-5-oxo-3-phenyl-11b-propyl-3,5,6,11b-tetrahydro-2H-oxazolo[3',2':1,2]pyrido[3,4-b]indole (1374399-79-7) → (R)-2-[(R)-2-hydroxy-1-phenylethyl]-1-propyl-1,2,3,4-tetrahydropyrido[3,4-b]indole (1374399-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride; aluminum (III) chloride / tetrahydrofuran / 4 h / -33 - 20 °C

2: ammonia; sodium / tetrahydrofuran / 0.17 h / -33 °C

With aluminum (III) chloride; lithium aluminium tetrahydride; ammonia; sodium; In tetrahydrofuran;

DOI:10.1002/ejoc.201101718

upstream raw materials:

1-benzyl-2-butanoyl-3-indoleacetic acid

D-2-phenylglycinol

Downstream raw materials:

(R)-9-benzyl-2-[(R)-2-hydroxy-1-phenylethyl]-1-propyl-1,2,3,4-tetrahydropyrido[3,4-b]indole

(S)-9-benzyl-2-[(R)-2-hydroxy-1-phenylethyl]-1-propyl-1,2,3,4-tetrahydropyrido[3,4-b]indole

(R)-2-[(R)-2-hydroxy-1-phenylethyl]-1-propyl-1,2,3,4-tetrahydropyrido[3,4-b]indole