methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate

Base Information

• Chemical Name: methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate
• CAS No.: 1266228-99-2
• Molecular Formula: C₂₆H₄₄N₄O₆
• Molecular Weight: 508.659
• Mol file: 1266228-99-2.mol

Synonyms:methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate

Chemical Property of methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate

There total 5 articles about methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate 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:

(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetic acid (894789-27-6) + methyl (3S,8aR)-octahydropyrrolo[1,2-a]pyrazine-3-carboxylate dihydrochloride → methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate (1266228-99-2)

Guidance literature:

With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; at 20 ℃; for 4h; Cooling with ice;

Reference yield:

methyl (3S,8aR)-2-benzyloctahydropyrrolo[1,2-a]pyrazine-3-carboxylate (1266228-97-0) → methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate (1266228-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol / 10 h / 20 °C

2: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; 4-methyl-morpholine / tetrahydrofuran / 4 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; palladium 10% on activated carbon; hydrogen; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; methanol;

DOI:10.1021/jm301674z

Reference yield:

D-pyrrolidone-5-carboxylic acid (4042-36-8) → methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate (1266228-99-2)

Guidance literature:

Multi-step reaction with 5 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 3 h / 0 - 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 60 °C

3: triethylamine / toluene / 5 h / 0 - 90 °C

4: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol / 10 h / 20 °C

5: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; 4-methyl-morpholine / tetrahydrofuran / 4 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; methanol; toluene; acetonitrile;

DOI:10.1021/jm301674z

upstream raw materials:

(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetic acid

D-pyrrolidone-5-carboxylic acid

(R)-5-oxopyrrolidine-2-carboxylic acid benzylamide

1-phenyl-N-[(2R)-pyrrolidin-2-ylmethyl]methanamine

Downstream raw materials:

C₃₃H₅₁N₅O₅

C₃₇H₅₃N₅O₅

C₃₃H₅₁N₅O₅

C₃₄H₅₁N₅O₆