6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester
• CAS No.: 1010073-27-4
• Molecular Formula: C₂₃H₃₀N₂O₃
• Molecular Weight: 382.503
• Mol file: 1010073-27-4.mol

Synonyms:6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester

Chemical Property of 6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester

There total 8 articles about 6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester 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:

(6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2,5]octane-6-carboxylic acid (791834-47-4) + 3-phenyl-3-pyrroline (52906-59-9) → 6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester (1010073-27-4)

Guidance literature:

With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jm061344o

Reference yield:

(S)-2-benzylamino-succinic acid 1-benzyl ester 4-tert-butyl ester (791834-41-8) → 6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester (1010073-27-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / K₂CO₃; NaI / acetonitrile / 16 h / 81 °C

2: 96 percent / NaI / acetone / 16 h / 20 °C

3: 72 percent / LiHMDS / tetrahydrofuran / 4 h / -78 - -30 °C

4: 93 percent / 28 h / 65 °C

5: 98 percent / palladium(II) acetate / diethyl ether / -20 - 20 °C

6: 98 percent / H₂ / Pd/BaSO₄ / methanol / 3 h / 20 °C

7: benzotriazol-1-yloxytris(dimethylamino)phosphonium*PF₆^(1-); 4-methylmorpholine / dimethylformamide / 2 h / 20 °C

With 4-methyl-morpholine; hydrogen; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; sodium iodide; lithium hexamethyldisilazane; Pd-BaSO₄; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jm061344o

Reference yield:

2-benzyl 3-tert-butyl (2S,3S)-1-benzyl-5-methylenepiperidine-2,3-dicarboxylate (791834-44-1) → 6-(3-phenyl-2,5-dihydro-pyrrole-1-carbonyl)-5-aza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester (1010073-27-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / 28 h / 65 °C

2: 98 percent / palladium(II) acetate / diethyl ether / -20 - 20 °C

3: 98 percent / H₂ / Pd/BaSO₄ / methanol / 3 h / 20 °C

4: benzotriazol-1-yloxytris(dimethylamino)phosphonium*PF₆^(1-); 4-methylmorpholine / dimethylformamide / 2 h / 20 °C

With 4-methyl-morpholine; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Pd-BaSO₄; palladium diacetate; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jm061344o

upstream raw materials:

(6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2,5]octane-6-carboxylic acid

3-phenyl-3-pyrroline

(S)-2-benzylamino-succinic acid 1-benzyl ester 4-tert-butyl ester

2-benzyl 3-tert-butyl (2S,3S)-1-benzyl-5-methylenepiperidine-2,3-dicarboxylate

Downstream raw materials:

C₂₅H₃₂N₂O₅