(S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione

Base Information

• Chemical Name: (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione
• CAS No.: 1621189-50-1
• Molecular Formula: C₁₄H₁₈N₂S
• Molecular Weight: 246.376

Synonyms:(S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione

Chemical Property of (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione

Chemical Property:

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Technology Process of (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione

There total 10 articles about (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione 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: 48.0%

(7aS,7'aS,E)-2,2'-bis[(R)-1-phenylethyl]-1,1',2,2',5,5',6,6',7,7',7a,7'a-dodecahydro-3,3'-bipyrrolo[1,2-c]imidazolylidene (1621189-48-7) → (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione (1621189-50-1)

Guidance literature:

With sulfur; In benzene-d6; at 20 ℃; for 2h; Glovebox; Schlenk technique; Inert atmosphere;

DOI:10.1055/s-0033-1340215

Reference yield:

1,1'-Thiocarbonyldiimidazole (6160-65-2) + (1R)-1-phenyl-N-(((S)-pyrrolidin-2-yl)methyl)ethanamine (67715-14-4) → (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione (1621189-50-1)

Guidance literature:

In 1,2-dichloro-benzene; at 185 ℃; for 6h;

DOI:10.1016/j.tetlet.2016.03.036

Reference yield:

(2S)-pyrrolidine-2-carboxylic acid N-((1R)-1-phenyl-ethyl)-amide (149673-13-2,149673-15-4,149673-17-6,149673-19-8) → (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione (1621189-50-1)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 15 h / Reflux; Inert atmosphere; Schlenk technique

2: ammonium hexafluorophosphate / 0.08 h / 145 °C / Microwave irradiation; Inert atmosphere; Schlenk technique

3: potassium tert-butylate / tetrahydrofuran / 0.75 h / 20 °C / Schlenk technique; Glovebox; Inert atmosphere

4: sulfur / benzene-d6 / 2 h / 20 °C / Glovebox; Schlenk technique; Inert atmosphere

With ammonium hexafluorophosphate; lithium aluminium tetrahydride; potassium tert-butylate; sulfur; In tetrahydrofuran; benzene-d6;

DOI:10.1055/s-0033-1340215

upstream raw materials:

(7aS,7'aS,E)-2,2'-bis[(R)-1-phenylethyl]-1,1',2,2',5,5',6,6',7,7',7a,7'a-dodecahydro-3,3'-bipyrrolo[1,2-c]imidazolylidene

N-Benzyloxycarbonyl-L-proline

(R,S)-2-(1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid benzyl ester

(2S)-pyrrolidine-2-carboxylic acid N-((1R)-1-phenyl-ethyl)-amide

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