(5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione

Base Information

• Chemical Name: (5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione
• CAS No.: 1309455-11-5
• Molecular Formula: C₁₆H₂₀N₂O₃
• Molecular Weight: 288.346
• Mol file: 1309455-11-5.mol

Synonyms:(5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione

Chemical Property of (5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione

There total 6 articles about (5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-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: 87.0%

(3S,5R)-1-benzyl-5-(hydroxymethyl)-3-isopropylpiperazin-2-one + 1,1'-carbonyldiimidazole (530-62-1) → (5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione (1309455-11-5)

Guidance literature:

In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2021.127961

Reference yield: 67.0%

(S)-O-t-butyl-N-[1-(allylbenzylamino)-3-methyl-1-oxobutan-2-yl]carbamate (1309455-02-4) → (5S,8aS)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione (1309455-22-8) + (5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione (1309455-11-5)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); copper dichloride; In N,N-dimethyl-formamide; at 100 ℃; for 24h; optical yield given as %de;

DOI:10.1002/adsc.201000889

Reference yield:

C23H35BrN2O4 → (5S,8aR)-7-benzyl-5-isopropyl-8,8a-dihydro-1H-oxazolo-[3,4-a]pyrazine-3,6(5H,7H)-dione (1309455-11-5)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / water; 1,4-dioxane / 12 h / 20 °C

2: sodium carbonate / ethanol / 10 h / 20 °C

3: dichloromethane / 3 h / 20 °C

With hydrogenchloride; sodium carbonate; In 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1016/j.bmcl.2021.127961

upstream raw materials:

Allylbenzylamine

t-Boc-L-valine

(S)-O-t-butyl-N-[1-(allylbenzylamino)-3-methyl-1-oxobutan-2-yl]carbamate

(R)-4-(Benzylamino-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester