(3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane

Base Information

Chemical Name:(3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane
CAS No.:208455-27-0
Molecular Formula:C₂₀H₂₈N₂O₃
Molecular Weight:344.454
Hs Code.:

Synonyms:(3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane

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Chemical Property of (3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane

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Technology Process of (3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane

There total 6 articles about (3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane 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: 81.0%

: 208455-24-7
(3S,6S,9S)-1-aza-2-oxo-3-aminocarbonyl-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane

: 208455-27-0
(3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane

Guidance literature:: With sodium hydroxide; benzyltrimethylammonium tribromide; In water; acetonitrile; at 20 ℃; for 12h;
DOI:10.1016/S0040-4020(98)00207-5

Reference yield:

: 178813-27-9
(2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester

: 208455-27-0
(3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 6 steps

1: 52 percent / DCC; 4-DMAP / tetrahydrofuran / 12 h / 20 °C

2: 100 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

3: 75 percent / NaBr / acetone / 4 h / Heating

4: NaH / tetrahydrofuran / 16 h / 0 °C

5: 70 percent / NaCN; ammonia / methanol / 96 h / 60 °C

6: 81 percent / NaOH; benzyltrimethylammonium tribromide / acetonitrile; H₂O / 12 h / 20 °C

With dmap; sodium hydroxide; benzyltrimethylammonium tribromide; sodium cyanide; ammonia; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; sodium bromide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; 1: Acylation / 2: mesylation / 3: Substitution / 4: Cyclization / 5: ammonolysis / 6: Hoffman reaction;
DOI:10.1016/S0040-4020(98)00207-5

Reference yield:

: 208455-18-9
(2S,5S)-1-[(2S,R)-methoxycarbonyl-3-phenyl-propionyl]-5-(2-bromoethyl)pyrrolidine-2-carboxylic acid tert-butyl ester

: 208455-27-0
(3R,6S,9S)-1-aza-2-oxo-3-amino-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 3 steps

1: NaH / tetrahydrofuran / 16 h / 0 °C

2: 70 percent / NaCN; ammonia / methanol / 96 h / 60 °C

3: 81 percent / NaOH; benzyltrimethylammonium tribromide / acetonitrile; H₂O / 12 h / 20 °C

With sodium hydroxide; benzyltrimethylammonium tribromide; sodium cyanide; ammonia; sodium hydride; In tetrahydrofuran; methanol; water; acetonitrile; 1: Cyclization / 2: ammonolysis / 3: Hoffman reaction;
DOI:10.1016/S0040-4020(98)00207-5