3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione

Base Information

• Chemical Name: 3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione
• CAS No.: 120417-18-7
• Molecular Formula: C₁₃H₁₄N₂O₃
• Molecular Weight: 246.266
• Mol file: 120417-18-7.mol

Synonyms:3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione

Chemical Property of 3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione

There total 10 articles about 3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione 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: 67.0%

(S)-3-<2-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-1-phenylethyl>-6-methyl-3,6-diazabicyclo<3.1.0>hexane-2,4-dione (127381-60-6) → 3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione (120417-18-7)

Guidance literature:

In tetrahydrofuran; acetic acid; at 55 ℃;

DOI:10.1021/jo00270a008

Reference yield:

(2S)-2-phenylglycinol (20989-17-7) → 3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione (120417-18-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 51 percent / CH₂Cl₂ / Ambient temperature

2: 88 percent / diethyl ether / 0 °C

3: 33 percent / NaOAc, Ac₂O / 120 °C

4: 87 percent / toluene / Ambient temperature

5: 78 percent / dioxane / Irradiation

6: 67 percent / aq. acetic acid; tetrahydrofuran / 55 °C

With sodium acetate; acetic anhydride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; acetic acid; toluene;

DOI:10.1021/jo00270a008

Reference yield:

-4-<<2-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-1-phenylethyl>amino>-4-oxo-2-butenoic acid (120417-14-3) → 3-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-3,6-diaza-bicyclo[3.1.0]hexane-2,4-dione (120417-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 33 percent / NaOAc, Ac₂O / 120 °C

2: 87 percent / toluene / Ambient temperature

3: 78 percent / dioxane / Irradiation

4: 67 percent / aq. acetic acid; tetrahydrofuran / 55 °C

With sodium acetate; acetic anhydride; In tetrahydrofuran; 1,4-dioxane; acetic acid; toluene;

DOI:10.1021/jo00270a008

upstream raw materials:

(S)-3-<2-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-1-phenylethyl>-6-methyl-3,6-diazabicyclo<3.1.0>hexane-2,4-dione

(2S)-2-phenylglycinol

-4-<<2-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-1-phenylethyl>amino>-4-oxo-2-butenoic acid

5-<(S)-2-<<(1,1-Dimethylethyl)dimethylsilyll>oxy>-1-phenylethyl>-3a,6a-dihydro-1-methylpyrrolo<3,4-d>-1,2,3-triazole-4,6(1H,5H)-dione

Downstream raw materials:

Acrylic acid (S)-2-(6-methyl-2,4-dioxo-3,6-diaza-bicyclo[3.1.0]hex-3-yl)-2-phenyl-ethyl ester