(6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

Base Information

Chemical Name:(6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene
CAS No.:173395-77-2
Molecular Formula:C₂₇H₃₁N₃O₅
Molecular Weight:477.56
Hs Code.:

(6R,9S)-1-aza-4-benzyl-3-<<N-(carbobenzyloxy)-L-alanyl>amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

Synonyms:(6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

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Chemical Property of (6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

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Technology Process of (6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

There total 10 articles about (6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene 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: 91.0%

: 173395-76-1
(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

: 173395-77-2
(6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

Guidance literature:: With sulfuric acid; In tetrahydrofuran; Ambient temperature;
DOI:10.1021/jo00130a015

Reference yield:

: (2S)-2-<(benzyloxy)methyl>-5-methoxy-1-(3-phenyl-4-pentenoyl)pyrrolidine

: 173395-77-2
(6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / TiCl₄ / CH₂Cl₂ / Ambient temperature

2: 78 percent / H₂, NaOMe / 5percent Pd/C / methanol

3: 90 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

4: 63 percent / n-BuLi, diisopropylamine, O₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

5: 45 percent / NH₃ / methanol / 1.) 0 deg C, 2.) room temperature, 3 d

6: 67 percent / HOBt, EDCI / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, overnight

7: 91 percent / 2 N H₂SO₄ / tetrahydrofuran / Ambient temperature

With n-butyllithium; sulfuric acid; ammonia; hydrogen; oxygen; sodium methylate; titanium tetrachloride; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jo00130a015

Reference yield:

: (9S)-1-aza-4-(chlorobenzyl)-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>nonane

: 173395-77-2
(6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / H₂, NaOMe / 5percent Pd/C / methanol

2: 90 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

3: 63 percent / n-BuLi, diisopropylamine, O₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

4: 45 percent / NH₃ / methanol / 1.) 0 deg C, 2.) room temperature, 3 d

5: 67 percent / HOBt, EDCI / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, overnight

6: 91 percent / 2 N H₂SO₄ / tetrahydrofuran / Ambient temperature

With n-butyllithium; sulfuric acid; ammonia; hydrogen; oxygen; sodium methylate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jo00130a015