(3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline

Base Information

• Chemical Name: (3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline
• CAS No.: 1242161-78-9
• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.364

Synonyms:(3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline

Chemical Property of (3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline

Chemical Property:

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Technology Process of (3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline

There total 1 articles about (3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline 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: 52.0%

D-2-phenylglycinol (56613-80-0) + 1-formyl-4,5-dimethoxyphenylacetic acid methyl ester (124201-24-7) → C19H19NO4 (1242161-86-9) + (3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline (1242161-78-9)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 18h; diastereoselective reaction; Reflux; Molecular sieve;

DOI:10.1002/ejoc.201000473

Reference yield: 82.0%

(3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline (1242161-78-9) + ethylmagnesium bromide (925-90-6) → (1S)-1-ethyl-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethoxy-3-oxo-1,2,3,4-tetrahydroisoquinoline (1242161-88-1)

Guidance literature:

In tetrahydrofuran; at 5 ℃; for 6h;

DOI:10.1002/ejoc.201000473

Reference yield: 67.0%

(3R,10bS)-8,9-dimethoxy-5-oxo-3-phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline (1242161-78-9) + phenylmagnesium chloride (100-59-4) → C19H19NO4 (1242161-79-0) + (1S)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethoxy-3-oxo-1-phenyl-1,2,3,4-tetrahydroisoquinoline (1242161-89-2)

Guidance literature:

In tetrahydrofuran; at 5 ℃; for 1h;

DOI:10.1002/ejoc.201000473

upstream raw materials:

D-2-phenylglycinol

1-formyl-4,5-dimethoxyphenylacetic acid methyl ester

Downstream raw materials:

(1S)-1-ethyl-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethoxy-3-oxo-1,2,3,4-tetrahydroisoquinoline

C₁₉H₁₉NO₄

(1S)-1-[2-(1,3-dioxan-2-yl)ethyl]-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethoxy-3-oxo-1,2,3,4-tetrahydroisoquinoline

(1S)-2-[(1R)-2-hydroxy-1-phenylethyl]-6,7-dimethoxy-3-oxo-1-phenyl-1,2,3,4-tetrahydroisoquinoline

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