tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Base Information

Chemical Name:tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate
CAS No.:1630984-80-3
Molecular Formula:C₂₇H₂₈N₄O₄
Molecular Weight:472.544
Hs Code.:

Synonyms:tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

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Chemical Property of tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

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Technology Process of tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

There total 3 articles about tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-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: 50.0%

: 84713-20-2
benzyl N-vinylcarbamate

: 1630984-76-7
tert-butyl 2-cyano-4-nitro-1H-pyrrole-1-carboxylate

: 100-52-7
benzaldehyde

: 1630984-80-3
tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Guidance literature:: tert-butyl 2-cyano-4-nitro-1H-pyrrole-1-carboxylate; With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 20.5h; under 760.051 Torr;

benzaldehyde; With C₃₂H₁₉Cl₂O₄P; In dichloromethane; at 20 ℃; for 0.666667h; Inert atmosphere;

benzyl N-vinylcarbamate; In dichloromethane; at 0 - 20 ℃; for 1.33h; enantioselective reaction; Inert atmosphere;
DOI:10.1002/adsc.201400093

Reference yield:

: 4513-94-4
1H-pyrrole-2-carbonitrile

: 1630984-80-3
tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: acetic anhydride; nitric acid / 4 h / -40 °C / Inert atmosphere

2.1: triethylamine; dmap / dichloromethane / 4 h / 20 °C / Inert atmosphere

3.1: hydrogen; palladium on activated charcoal / ethyl acetate / 20.5 h / 20 °C / 760.05 Torr

3.2: 0.67 h / 20 °C / Inert atmosphere

3.3: 1.33 h / 0 - 20 °C / Inert atmosphere

With dmap; palladium on activated charcoal; hydrogen; nitric acid; acetic anhydride; triethylamine; In dichloromethane; ethyl acetate;
DOI:10.1002/adsc.201400093

Reference yield:

: 59027-78-0
4-nitro-1H-pyrrole-2-carbonitrile

: 1630984-80-3
tert-butyl (5S,7S)-7-(((benzyloxy)carbonyl)amino)-2-cyano-5-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine; dmap / dichloromethane / 4 h / 20 °C / Inert atmosphere

2.1: hydrogen; palladium on activated charcoal / ethyl acetate / 20.5 h / 20 °C / 760.05 Torr

2.2: 0.67 h / 20 °C / Inert atmosphere

2.3: 1.33 h / 0 - 20 °C / Inert atmosphere

With dmap; palladium on activated charcoal; hydrogen; triethylamine; In dichloromethane; ethyl acetate;
DOI:10.1002/adsc.201400093