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

Base Information

• Chemical Name: (S)-N-[(1R)-1-phenylethyl]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide
• CAS No.: 1636138-25-4
• Molecular Formula: C₂₃H₂₈N₂O₂S
• Molecular Weight: 396.554
• Mol file: 1636138-25-4.mol

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

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

There total 8 articles about (S)-N-[(1R)-1-phenylethyl]-2-(tert-butoxycarbonyl)-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: 50.0%

(S)-N-[(1R)-1-phenylethyl]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide (1636138-21-0) → (S)-N-[(1R)-1-phenylethyl]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (1636138-25-4)

Guidance literature:

With Lawessons reagent; In toluene; at 110 ℃; for 6h;

DOI:10.3987/COM-14-13029

Reference yield:

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

Guidance literature:

Multi-step reaction with 3 steps

1.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 24 h / 25 °C / 37.5 Torr

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

2.2: 16 h / 25 °C

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

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

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]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (1636138-25-4)

Guidance literature:

Multi-step reaction with 5 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

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

Downstream raw materials:

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