(1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 1068158-37-1
• Molecular Formula: C₁₅H₂₁N
• Molecular Weight: 215.338
• Mol file: 1068158-37-1.mol

Synonyms:(1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

There total 9 articles about (1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline 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: 90.0%

1-cyclohexyl-3,4-dihydroisoquinoline (65071-52-5) → (1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (1068158-37-1)

Guidance literature:

With silver hexafluoroantimonate; C₃₁H₃₆ClN₂O₂RhS; hydrogen; In water; isopropyl alcohol; at 20 ℃; for 24h; under 37503.8 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1021/ja8050958

Reference yield:

cyclohexylmagnesium bromide (931-50-0) → (1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (1068158-37-1)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 0.25 h / 0 - 20 °C

2: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere

3: titanium(IV) isopropylate; toluene-4-sulfonic acid; iodine / toluene / Inert atmosphere; Glovebox

4: hydrogen / tetrahydrofuran; toluene / 17 h / 30 °C / 45603.1 Torr / Autoclave

With titanium(IV) isopropylate; hydrogen; iodine; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/anie.201611181

Reference yield:

1-cyclohexyl-3,4-dihydroisoquinoline (65071-52-5) → (R)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (1085538-45-9) + (1S)-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (1068158-37-1)

Guidance literature:

With silver hexafluoroantimonate; C₃₁H₃₆ClN₂O₂RhS; hydrogen; In dichloromethane; water; at 20 ℃; for 4h; under 15001.5 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1021/ja8050958

upstream raw materials:

1-cyclohexyl-3,4-dihydroisoquinoline

cyclohexylmagnesium bromide

3,4-dihydroisoquinolin-1(2H)-one

phenethylamine

Refernces

• 1、 Zhou, Huan,Liu, Yuan,Yang, Suhua,Zhou, Le,Chang, Mingxin. "One-Pot N-Deprotection and Catalytic Intramolecular Asymmetric Reductive Amination for the Synthesis of Tetrahydroisoquinolines". supporting information. p. 2725 - 2729. Retrieved 2017/02/26.