(3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate

Base Information

Chemical Name:(3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate
CAS No.:346441-83-6
Molecular Formula:C₁₈H₂₂N₂O₅
Molecular Weight:346.383
Hs Code.:

Synonyms:(3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate

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Chemical Property of (3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate

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Technology Process of (3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate

There total 5 articles about (3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-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: 74.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 346441-82-5
(2R,7R)-5-(1,3-dioxolane)-2,8-bis[N-benzyloxycarbonylamino]nonane-1,9-dioic acid dimethyl ester

: 346441-83-6
(3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate

: (R)-5-((R)-3-Benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: (2R,7R)-5-(1,3-dioxolane)-2,8-bis[N-benzyloxycarbonylamino]nonane-1,9-dioic acid dimethyl ester; With hydrogen; palladium on activated charcoal; In hydrogenchloride; methanol; for 24h; under 3620.04 Torr;

With sodium hydrogencarbonate; In 1,4-dioxane; water; for 4h; pH=8 - 9;

benzyl chloroformate; In 1,4-dioxane; water; for 3h;
DOI:10.1016/S0040-4039(01)00409-9

Reference yield:

: 71022-90-7
diethyl 2,2'-(1,3-dioxolane-2,2-diyl)diacetate

: 346441-83-6
(3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 70 percent Spectr_. / DIBAL / toluene / 1.17 h / -78 °C

2.1: 72 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

3.1: 95 percent / H₂ / Rh(I)(COD)(R,R) Et-DUPHOS / methanol / 24 h / 3620.04 Torr

4.1: H₂ / 10 percent Pd/C / methanol; aq. HCl / 24 h / 3620.04 Torr

4.2: NaHCO₃ / dioxane; H₂O / 4 h / pH 8 - 9

4.3: 74 percent / dioxane; H₂O / 3 h

With hydrogen; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; Rh(I)(COD)(R,R)-Et-DUPHOS; In hydrogenchloride; methanol; dichloromethane; toluene; 2.1: Horner-Emmons olefination;
DOI:10.1016/S0040-4039(01)00409-9

Reference yield:

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 346441-83-6
(3R,6R,9R) methyl 2-oxo-3-[N-(benzoxycarbonyl)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 76 percent / BF₃*Et₂O / benzene / 24 h / Heating

2.1: 70 percent Spectr_. / DIBAL / toluene / 1.17 h / -78 °C

3.1: 72 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

4.1: 95 percent / H₂ / Rh(I)(COD)(R,R) Et-DUPHOS / methanol / 24 h / 3620.04 Torr

5.1: H₂ / 10 percent Pd/C / methanol; aq. HCl / 24 h / 3620.04 Torr

5.2: NaHCO₃ / dioxane; H₂O / 4 h / pH 8 - 9

5.3: 74 percent / dioxane; H₂O / 3 h

With boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; Rh(I)(COD)(R,R)-Et-DUPHOS; In hydrogenchloride; methanol; dichloromethane; toluene; benzene; 3.1: Horner-Emmons olefination;
DOI:10.1016/S0040-4039(01)00409-9