methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-carboxylate

Base Information

• Chemical Name: methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-carboxylate
• CAS No.: 1452400-41-7
• Molecular Formula: C₁₇H₂₂N₂O₂
• Molecular Weight: 286.374
• Mol file: 1452400-41-7.mol

Synonyms:methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-carboxylate

Chemical Property of methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-carboxylate

There total 10 articles about methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-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:

Methyl 2,3-dibromopropionate (1729-67-5) + 1-[(1R,3R,5R)-2-azabicyclo[3.1.0]hex-3-yl]-N-benzylmethanamine (1266231-39-3) → methyl (1aR,4S,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-4-carboxylate (1266231-40-6) + methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-carboxylate (1452400-41-7)

Guidance literature:

With triethylamine; In toluene; at 90 ℃; for 18h;

DOI:10.1016/j.bmc.2013.07.020

Reference yield:

tert-butyl (1R,3R,5R)-3-formyl-2-azabicyclo[3.1.0]hexane-2-carboxylate (1148048-42-3) → methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-carboxylate (1452400-41-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 1.5 h / 20 °C

2: hydrogenchloride / ethyl acetate / 18 h / 20 °C

3: triethylamine / toluene / 18 h / 90 °C

With hydrogenchloride; sodium tris(acetoxy)borohydride; triethylamine; In tetrahydrofuran; ethyl acetate; toluene;

DOI:10.1016/j.bmc.2013.07.020

Reference yield:

1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate (144978-12-1,128811-48-3,144978-35-8,251924-83-1) → methyl (1aR,4R,6aR,7aR)-5-benzyloctahydro-1H-cyclopropa[4,5] pyrrolo[1,2-a]pyrazine-4-carboxylate (1452400-41-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium triethylborohydride / toluene; tetrahydrofuran / 1 h / -78 °C

1.2: 3 h / 20 °C

2.1: diethylzinc / toluene / 0.5 h / -40 °C

2.2: 4.5 h / -40 - 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C

4.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / ethyl acetate / 1 h / 0 - 20 °C

5.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 1.5 h / 20 °C

6.1: hydrogenchloride / ethyl acetate / 18 h / 20 °C

7.1: triethylamine / toluene / 18 h / 90 °C

With hydrogenchloride; lithium aluminium tetrahydride; diethylzinc; sulfur trioxide pyridine complex; sodium tris(acetoxy)borohydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethyl acetate; toluene;

DOI:10.1016/j.bmc.2013.07.020

upstream raw materials:

tert-butyl (1R,3R,5R)-3-formyl-2-azabicyclo[3.1.0]hexane-2-carboxylate

1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate

1-tert-butyl 2-ethyl (2R)-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-pyrrole-1-carboxylate

Downstream raw materials:

tert-butyl [(1S)-2-{[(1S)-1-cyclohexyl-2-{(1aR,4S,6aR,7aR)-4-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]octahydro-5H-cyclopropa[4,5]pyrrolo[1,2-a]pyrazin-5-yl}-2-oxoethyl]amino}-1-methyl-2-oxoethyl]methylcarbamate