(6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane

Base Information

• Chemical Name: (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane
• CAS No.: 325460-75-1
• Molecular Formula: C₁₅H₁₉NO₂
• Molecular Weight: 245.321
• Mol file: 325460-75-1.mol

Synonyms:(6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane

Chemical Property of (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane

There total 6 articles about (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[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: 93.0%

(6R)-1-aza-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]nonane (325460-61-5) → (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane (325460-75-1)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(00)00886-3

Reference yield:

(R)-N-(benzoyloxycarbonyl)-allylproline methyl ester (157662-40-3) → (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane (325460-75-1)

Guidance literature:

Multi-step reaction with 6 steps

1: O₃ / CH₂Cl₂ / 1.25 h / -78 °C

2: 9.96 g / CH₂Cl₂ / -78 - 20 °C

3: 61 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -78 - -20 °C

4: H₂ / Pd/BaSO₄ / methanol

5: 2.4 g / Et₃N / toluene / 21 h / Heating

6: 93 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

With lithium borohydride; boron trifluoride diethyl etherate; hydrogen; ozone; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1: ozonolysis / 2: Wittig reaction / 3: Addition / 4: Hydrogenolysis / 5: cyclocondensation / 6: Reduction;

DOI:10.1016/S0040-4020(00)00886-3

Reference yield:

(R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester (157662-41-4) → (6R)-1-aza-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]nonane (325460-75-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 9.96 g / CH₂Cl₂ / -78 - 20 °C

2: 61 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -78 - -20 °C

3: H₂ / Pd/BaSO₄ / methanol

4: 2.4 g / Et₃N / toluene / 21 h / Heating

5: 93 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

With lithium borohydride; boron trifluoride diethyl etherate; hydrogen; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1: Wittig reaction / 2: Addition / 3: Hydrogenolysis / 4: cyclocondensation / 5: Reduction;

DOI:10.1016/S0040-4020(00)00886-3

upstream raw materials:

(6R)-1-aza-6-carbomethoxy-4-phenyl-2-oxobicyclo[4.3.0]nonane

(R)-N-(benzoyloxycarbonyl)-allylproline methyl ester

(R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester

(2R)-2-[2'-(phenyl)-3'-(carbomethoxy)-propyl]proline methyl ester

Downstream raw materials:

(6R)-1-aza-6-[(tert-butyldimethylsiloxy)methyl]-3-hydroxy-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

(6R)-1-aza-3-amino-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

(6R,12S)-1-aza-3-(pyroglutamylamino)-6-formyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

(6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene