(1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine

Base Information

• Chemical Name: (1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine
• CAS No.: 142605-22-9
• Molecular Formula: C₂₀H₂₁NOS
• Molecular Weight: 323.459

Synonyms:(1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine

Chemical Property of (1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine

Chemical Property:

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Technology Process of (1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine

There total 8 articles about (1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine 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: 80.0%

methyl magnesium iodide (917-64-6) + (3R,11bS)-3-phenyl-2,3,5,6-tetrahydro-11bH-benzo<4,5>thieno<2,3-c>oxazolo<3,2-a>pyridine (142605-19-4) → (1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine (142605-22-9) + (1R,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine (142605-22-9)

Guidance literature:

In diethyl ether; at -78 ℃; for 3h; Yields of byproduct given;

DOI:10.1248/cpb.39.3338

Reference yield: 80.0%

methyl magnesium iodide (917-64-6) + (3R,11bS)-3-phenyl-2,3,5,6-tetrahydro-11bH-benzo<4,5>thieno<2,3-c>oxazolo<3,2-a>pyridine (142605-19-4) → (1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine (142605-22-9) + (1R,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine (142605-22-9)

Guidance literature:

In diethyl ether; at -78 ℃; for 3h; Yields of byproduct given;

DOI:10.1248/cpb.39.3338

Reference yield:

3-(2-bromoethyl)benzothiophene (19985-73-0) → (1R,1'R)-2-(2-hydroxy-1-phenylethyl)-1-methyl-1,2,3,4-tetrahydrobenzo<4,5>thieno<2,3-c>pyridine (142605-22-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) BuLi / 1.) hexane, THF, -78 deg C, 45 min, 2.) hexane, THF, -78 deg C, 30 min

2: p-TsOH / diethyl ether; ethanol / 12 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / -78 °C

4: diethyl ether / 3 h / -78 °C

With n-butyllithium; toluene-4-sulfonic acid; triethylamine; In diethyl ether; ethanol; dichloromethane;

DOI:10.1248/cpb.39.3338

upstream raw materials:

methyl magnesium iodide

(3R,11bS)-3-phenyl-2,3,5,6-tetrahydro-11bH-benzo<4,5>thieno<2,3-c>oxazolo<3,2-a>pyridine

3-(2-bromoethyl)benzothiophene

2-formyl-3-(2-bromoethyl)benzothiophene

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