benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate
CAS No.:1474047-58-9
Molecular Formula:C₂₉H₄₃N₃O₅
Molecular Weight:513.678
Hs Code.:

Synonyms:benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate

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Chemical Property of benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate

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Technology Process of benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate

There total 7 articles about benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-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%

: 705949-07-1
C₁₆H₂₇NO₄

: 119020-03-0,141774-68-7
2-(S)-aminomethyl-pyrrolidine-1-carboxylic acid benzyl ester

: 1474047-58-9
benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate

Guidance literature:: C₁₆H₂₇NO₄; With triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; at -10 ℃; for 1h; Inert atmosphere;

2-(S)-aminomethyl-pyrrolidine-1-carboxylic acid benzyl ester; With 4-methyl-morpholine; In tetrahydrofuran; dichloromethane; at -10 - 20 ℃; for 20h; Inert atmosphere;
DOI:10.1055/s-0033-1339291

Reference yield:

: 7785-70-8,25766-18-1
(+)-α-pinene

: 1474047-58-9
benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium sulfite / 2 h

2.1: dmap / acetonitrile / 12 h / 20 °C

3.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C

4.1: triethylamine; isobutyl chloroformate / tetrahydrofuran; dichloromethane / 1 h / -10 °C / Inert atmosphere

4.2: 20 h / -10 - 20 °C / Inert atmosphere

With dmap; water; triethylamine; lithium hydroxide; sodium sulfite; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1055/s-0033-1339291

Reference yield:

: 1148-11-4
N-Benzyloxycarbonyl-L-proline

: 1474047-58-9
benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C

1.2: 4 h / 0 °C

2.1: triphenylphosphine; di-isopropyl azodicarboxylate; hydrogen azide / benzene / 0.83 h / 0 - 20 °C

3.1: triphenylphosphine; water / tetrahydrofuran / 12 h / 20 °C

4.1: triethylamine; isobutyl chloroformate / tetrahydrofuran; dichloromethane / 1 h / -10 °C / Inert atmosphere

4.2: 20 h / -10 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; hydrogen azide; di-isopropyl azodicarboxylate; water; triethylamine; triphenylphosphine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; benzene; 2.1: |Mitsunobu Displacement / 3.1: |Staudinger Azide Reduction;
DOI:10.1055/s-0033-1339291