Pyrrolo[1,2-a]pyrazine-1-carboxylicacid, octahydro-, (1S,8aS)-

Base Information

• Chemical Name: Pyrrolo[1,2-a]pyrazine-1-carboxylicacid, octahydro-, (1S,8aS)-
• CAS No.: 273223-57-7
• Molecular Formula: C₈H₁₄N₂O₂
• Molecular Weight: 170.211
• DSSTox Substance ID: DTXSID90467188
• Nikkaji Number: J1.280.595K
• Wikidata: Q82293999
• Mol file: 273223-57-7.mol

Synonyms:273223-57-7;(1S,8AS)-octahydropyrrolo[1,2-a]pyrazine-1-carboxylic acid;Pyrrolo[1,2-a]pyrazine-1-carboxylicacid, octahydro-, (1S,8aS)-;DTXSID90467188;(1S,8AS)-octahydropyrrolo[1,2-a]pyrazine-1-carboxylicacid;(8aalpha)-Octahydropyrrolo[1,2-a]pyrazine-1beta-carboxylic acid

Chemical Property of Pyrrolo[1,2-a]pyrazine-1-carboxylicacid, octahydro-, (1S,8aS)-

Chemical Property:

• PSA: 52.57000
• LogP: -0.22610
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 170.105527694
• Heavy Atom Count: 12
• Complexity: 196

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(NCCN2C1)C(=O)O
• Isomeric SMILES: C1C[C@H]2[C@H](NCCN2C1)C(=O)O

Technology Process of Pyrrolo[1,2-a]pyrazine-1-carboxylicacid, octahydro-, (1S,8aS)-

There total 10 articles about Pyrrolo[1,2-a]pyrazine-1-carboxylicacid, octahydro-, (1S,8aS)- 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: 62.0%

methyl octahydro-9S-pyrrolo[1,2-a]pyrazine-1S-carboxylate (273223-56-6) → octahydro-9S-pyrrolo[1,2-a]pyrazine-1S-carboxylic acid (273223-57-7)

Guidance literature:

With porcine liver esterase; In phosphate buffer; for 96h; pH=7.2;

DOI:10.3987/COM-99-S136

Reference yield:

(S)-benzyloxycarbonyl-proline acid chloride (61350-60-5,61350-62-7,89705-40-8,106709-50-6) → octahydro-9S-pyrrolo[1,2-a]pyrazine-1S-carboxylic acid (273223-57-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: diethyl ether / 2 h / 0 °C

2.1: 92 percent / silver benzoate; Et₃N / 0.67 h

3.1: NaHMDS / tetrahydrofuran / 1 h / -100 °C

3.2: 80 percent / trisyl azide / tetrahydrofuran / 5 h / -100 °C

4.1: 98 percent / triphenylphosphine / tetrahydrofuran / 24 h

5.1: 75 percent / CH₂Cl₂ / 2 h

6.1: 100 percent / 5 percent Pd/C / methanol / 0.42 h

7.1: 70 percent / Et₃N; Bu₄NI; DMAP / CH₂Cl₂ / 18 h / Heating

8.1: 40 percent / Lawesson's reagent / dioxane / 1.5 h / 95 °C

9.1: 80 percent / Raney nickel; hydrogen / propan-2-ol / 0.5 h / 1654.87 Torr

10.1: 62 percent / porcine liver esterase / aq. phosphate buffer / 96 h / pH 7.2

With Lawessons reagent; porcine liver esterase; dmap; hydrogen; sodium hexamethyldisilazane; silver benzoate; tetra-(n-butyl)ammonium iodide; nickel; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; phosphate buffer; diethyl ether; dichloromethane; isopropyl alcohol; 1.1: Substitution / 2.1: Oxidation / 3.1: Reduction / 3.2: Substitution / 4.1: Reduction / 5.1: Acylation / 6.1: Hydrogenolysis / 7.1: Cyclization / 8.1: Substitution / 9.1: Reduction / 10.1: Hydrolysis;

DOI:10.3987/COM-99-S136

Reference yield:

2-(S)-(2-diazo-1-oxoethyl)pyrrolidine-1-carboxylic acid benzyl ester (56633-71-7) → octahydro-9S-pyrrolo[1,2-a]pyrazine-1S-carboxylic acid (273223-57-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 92 percent / silver benzoate; Et₃N / 0.67 h

2.1: NaHMDS / tetrahydrofuran / 1 h / -100 °C

2.2: 80 percent / trisyl azide / tetrahydrofuran / 5 h / -100 °C

3.1: 98 percent / triphenylphosphine / tetrahydrofuran / 24 h

4.1: 75 percent / CH₂Cl₂ / 2 h

5.1: 100 percent / 5 percent Pd/C / methanol / 0.42 h

6.1: 70 percent / Et₃N; Bu₄NI; DMAP / CH₂Cl₂ / 18 h / Heating

7.1: 40 percent / Lawesson's reagent / dioxane / 1.5 h / 95 °C

8.1: 80 percent / Raney nickel; hydrogen / propan-2-ol / 0.5 h / 1654.87 Torr

9.1: 62 percent / porcine liver esterase / aq. phosphate buffer / 96 h / pH 7.2

With Lawessons reagent; porcine liver esterase; dmap; hydrogen; sodium hexamethyldisilazane; silver benzoate; tetra-(n-butyl)ammonium iodide; nickel; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; phosphate buffer; dichloromethane; isopropyl alcohol; 1.1: Oxidation / 2.1: Reduction / 2.2: Substitution / 3.1: Reduction / 4.1: Acylation / 5.1: Hydrogenolysis / 6.1: Cyclization / 7.1: Substitution / 8.1: Reduction / 9.1: Hydrolysis;

DOI:10.3987/COM-99-S136

upstream raw materials:

methyl octahydro-9S-pyrrolo[1,2-a]pyrazine-1S-carboxylate

(S)-benzyloxycarbonyl-proline acid chloride

2-(S)-(2-diazo-1-oxoethyl)pyrrolidine-1-carboxylic acid benzyl ester

(-)-(S)-2-methoxycarbonylmethylpyrrolidine-1-carboxylic acid benzyl ester

Refernces