(S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide

Base Information

• Chemical Name: (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide
• CAS No.: 1636138-33-4
• Molecular Formula: C₁₈H₂₀N₂S
• Molecular Weight: 296.436
• Mol file: 1636138-33-4.mol

Synonyms:

Chemical Property of (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide

There total 8 articles about (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide 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: 77.0%

(S)-N-[(1R)-1-phenylethyl]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (1636138-25-4) → (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (1636138-33-4)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 2h;

DOI:10.3987/COM-14-13029

Reference yield:

benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt (77497-97-3) → (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (1636138-33-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydrogencarbonate / water

2.1: dichloromethane / 2 h / 25 °C

3.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 24 h / 25 °C / 37.5 Torr

4.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.17 h

4.2: 16 h / 25 °C

5.1: Lawessons reagent / toluene / 6 h / 110 °C

6.1: trifluoroacetic acid / 2 h / 0 °C

With Lawessons reagent; 5%-palladium/activated carbon; hydrogen; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene;

DOI:10.3987/COM-14-13029

Reference yield:

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid (115962-35-1,144069-68-1,78879-20-6) → (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (1636138-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.17 h

1.2: 16 h / 25 °C

2.1: Lawessons reagent / toluene / 6 h / 110 °C

3.1: trifluoroacetic acid / 2 h / 0 °C

With Lawessons reagent; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; In tetrahydrofuran; toluene;

DOI:10.3987/COM-14-13029

upstream raw materials:

benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid

(R)-1-phenyl-ethyl-amine

L-Tic-OH