(1S,5S,7R,8R)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane

Base Information

Chemical Name:(1S*,5S*,7R*,8R*)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane
CAS No.:116237-10-6
Molecular Formula:C₂₅H₃₁NO₅
Molecular Weight:425.525
Hs Code.:

Synonyms:(1S*,5S*,7R*,8R*)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane

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Chemical Property of (1S*,5S*,7R*,8R*)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane

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Technology Process of (1S*,5S*,7R*,8R*)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane

There total 14 articles about (1S*,5S*,7R*,8R*)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane 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: 33.0%

: 17615-02-0
1-cyclohexyl-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one

: 116237-07-1,120294-20-4
(1S*,5S*,7R*,8R*)-8-<7-hydroxy-N-(m-methoxycarbonylbenzoyl)-3-azabicyclo<3.3.0>octanyl>carbaldehyde

: 116237-10-6
(1S*,5S*,7R*,8R*)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane

Guidance literature:: In tetrahydrofuran; at 80 ℃; for 3h;
DOI:10.1248/cpb.39.3175

Reference yield:

: 116237-04-8,120294-17-9
(1S*,5S*,7R*,8S*)-<7-acetoxy-N-benzyl-3-azabicyclo<3.3.0>oct-8-yl>methyl acetate

: 116237-10-6
(1S*,5S*,7R*,8R*)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) H₂ / 1.) Pd-C / 1.) ethanol, 50 deg C, 18 h, 2.) Et₃N, DMAP, 25 deg C, 12 h

2: 80 percent / HCl, methanol / 1 h / 25 °C

3: DCCD, DMSO

4: tetrahydrofuran / 4 h / Heating

With hydrogenchloride; methanol; hydrogen; dimethyl sulfoxide; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran;

Reference yield:

: 930-30-3
cyclopent-2-enone

: 116237-10-6
(1S*,5S*,7R*,8R*)-8-(3-cyclohexyl-3-oxo-1-propenyl)-7-hydroxy-N-m-methoxycarbonylbenzoyl-3-azabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 7 steps

1: TFA

2: 1.) toluene-p-sulfonyl-hydrazide, trifluroacetic acid, 2.) disodium ethylene glycolate in diethylene glycol / 1.) ethanol, reflux, 2 h, 2.) HMPA, reflux, 6 h

3: 57 percent / 72 h / 70 °C / Prins reaction

4: 1.) H₂ / 1.) Pd-C / 1.) ethanol, 50 deg C, 18 h, 2.) Et₃N, DMAP, 25 deg C, 12 h

5: 80 percent / HCl, methanol / 1 h / 25 °C

6: DCCD, DMSO

7: tetrahydrofuran / 4 h / Heating

With hydrogenchloride; methanol; disodium ethylene glycolate in diethylene glycol; hydrogen; dimethyl sulfoxide; toluene-4-sulfonic acid hydrazide; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran;