(2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Base Information

• Chemical Name: (2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester
• CAS No.: 111301-23-6
• Molecular Formula: C₂₁H₂₉N₃O₈
• Molecular Weight: 451.477

Synonyms:(2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Chemical Property of (2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

There total 10 articles about (2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl 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: 72.0%

(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester (111301-22-5) → (2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester (111301-23-6)

Guidance literature:

With hydrogen; Raney Ni (W-2); In ethanol; triethylamine; at 100 ℃; under 77572.2 Torr;

DOI:10.1016/S0040-4039(00)85425-8

Reference yield:

ethyl α-carbethoxyaminoacrylate (20620-36-4) → (2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester (111301-23-6)

Guidance literature:

Multi-step reaction with 10 steps

2: 1) LDA, 2) ZnCl₂ / 1) THF, -78 deg C, 2) THF, 0 deg C

3: H₂ / 10percent Pd/C / ethanol / 760 Torr

4: H₂ / 5percent Rh/C / ethyl acetate / 80 °C / 77572.2 Torr

5: K₂CO₃ / dimethylformamide / 80 °C

6: 1) H₂CrO₄, 2) K₂CO₃ / 1) acetone, room temp., 2) acetone, reflux

8: 79 percent / CSA, quinoline / benzene / Heating

9: 1) NOCl, 2) NaBH₃CN / 1) CH₃CN, CH₂Cl₂, -30 deg C; 2) MeOH, -30 to 0 deg C

10: 72 percent / H₂ / Raney Ni (W-2) / triethylamine; ethanol / 100 °C / 77572.2 Torr

With quinoline; camphor-10-sulfonic acid; hydrogen; chromic acid; sodium cyanoborohydride; potassium carbonate; nitrosylchloride; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; Rh on carbon; Raney Ni (W-2); In ethanol; ethyl acetate; triethylamine; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)85425-8

Reference yield:

5-Hydroxymethyl-2-methyl-4,5-dihydro-pyrrole-1,3-dicarboxylic acid 3-tert-butyl ester 1-ethyl ester (111301-17-8) → (2R,3aR,6S,7R,7aS)-7-Amino-6-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester (111301-23-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) LDA, 2) ZnCl₂ / 1) THF, -78 deg C, 2) THF, 0 deg C

2: H₂ / 10percent Pd/C / ethanol / 760 Torr

3: H₂ / 5percent Rh/C / ethyl acetate / 80 °C / 77572.2 Torr

4: K₂CO₃ / dimethylformamide / 80 °C

5: 1) H₂CrO₄, 2) K₂CO₃ / 1) acetone, room temp., 2) acetone, reflux

7: 79 percent / CSA, quinoline / benzene / Heating

8: 1) NOCl, 2) NaBH₃CN / 1) CH₃CN, CH₂Cl₂, -30 deg C; 2) MeOH, -30 to 0 deg C

9: 72 percent / H₂ / Raney Ni (W-2) / triethylamine; ethanol / 100 °C / 77572.2 Torr

With quinoline; camphor-10-sulfonic acid; hydrogen; chromic acid; sodium cyanoborohydride; potassium carbonate; nitrosylchloride; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; Rh on carbon; Raney Ni (W-2); In ethanol; ethyl acetate; triethylamine; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)85425-8

upstream raw materials:

(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

ethyl α-carbethoxyaminoacrylate

5-Hydroxymethyl-2-methyl-4,5-dihydro-pyrrole-1,3-dicarboxylic acid 3-tert-butyl ester 1-ethyl ester

(2R,3aR,7aR)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-4-oxo-2,3,3a,4,5,7a-hexahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

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