(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester
• CAS No.: 124665-33-4
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 124665-33-4.mol

Synonyms:(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

Chemical Property of (1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

There total 1 articles about (1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester 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: 91.8%

4-[(phenylmethoxy)methyl]-2-cyclohex-2-en-1-one (124665-32-3,118378-02-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester (124665-33-4)

Guidance literature:

In dichloromethane; at 4 ℃; for 6h; Irradiation;

DOI:10.1016/S0040-4020(01)83440-2

Reference yield:

(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester (124665-33-4) → C29H32N2O3Se (118378-12-4)

Guidance literature:

Multi-step reaction with 21 steps

1: amberlyst 15 / 2 h / 0 °C

2: benzene; diethyl ether / 0.58 h

3: pyridinium p-toluenesulfonate / acetone / 0.33 h / Ambient temperature

4: 84 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 46 h / Ambient temperature

5: sodium hydride / tetrahydrofuran / 6.5 h / Ambient temperature

6: triethylamine / 1.) 0 deg C, 1h; 2.) rt, 36h

7: potassium hydroxide / methanol; H₂O / 2.5 h / Heating

8: 87 percent / hydroxylamine hydrochloride, sodium acetate / methanol / 0.67 h / Heating

9: xylene / 0.83 h / 150 °C

10: sodium hydroxide / ethanol; H₂O / 7.25 h / Heating

11: 84 percent / H₂, (1S)-(+)-10-camphorsulfonic acid / palladium hydroxide on carbon / ethyl acetate / 22.5 h

12: 85 percent / N-ethyldiisopropylamine / 4-dimethylaminopyridine / CH₂Cl₂ / 1.) 0 deg C, 40 min; 2.) rt,1.33 h

13: lithium diisopropylamide / hexane; tetrahydrofuran / 1.) 0 deg C, 50 min; 2.) rt, 50 min

14: 83 percent / n-BuLi / hexane; tetrahydrofuran / 1.1 h / Ambient temperature

15: pyridinium p-toluenesulfonate / dimethylformamide / 0.83 h / Ambient temperature

16: sodium hydride / dimethylformamide / 1.25 h

17: 99 percent / acetic acid; tetrahydrofuran; propan-2-ol / 8.5 h / Ambient temperature

18: 88 percent / dicyclohexylcarbodiimide, pyridine, trifluoroacetic acid, DMSO / benzene / 4.5 h / Ambient temperature

19: 61 percent / (1S)-(+)-10-camphorsulfonic acid / methanol; toluene / 3 h / Ambient temperature

20: 8.9 percent / ethanethiol, sodium hydride / dimethylformamide / 1 h / 150 °C

21: 96 percent / tri-n-butylphosphine / tetrahydrofuran / 1.) 0 deg C, 10 min; 2.) rt, 35 min

With pyridine; potassium hydroxide; sodium hydroxide; n-butyllithium; Amberlyst 15; tributylphosphine; hydroxylamine hydrochloride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; (+)-10-camphorsulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; ethanethiol; lithium diisopropyl amide; dmap; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; xylene; benzene;

DOI:10.1016/S0040-4020(01)83440-2

Reference yield:

(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester (124665-33-4) → C30H35NO3 (124665-47-0)

Guidance literature:

Multi-step reaction with 20 steps

1: amberlyst 15 / 2 h / 0 °C

2: benzene; diethyl ether / 0.58 h

3: pyridinium p-toluenesulfonate / acetone / 0.33 h / Ambient temperature

4: 84 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 46 h / Ambient temperature

5: sodium hydride / tetrahydrofuran / 6.5 h / Ambient temperature

6: triethylamine / 1.) 0 deg C, 1h; 2.) rt, 36h

7: potassium hydroxide / methanol; H₂O / 2.5 h / Heating

8: 87 percent / hydroxylamine hydrochloride, sodium acetate / methanol / 0.67 h / Heating

9: xylene / 0.83 h / 150 °C

10: sodium hydroxide / ethanol; H₂O / 7.25 h / Heating

11: 84 percent / H₂, (1S)-(+)-10-camphorsulfonic acid / palladium hydroxide on carbon / ethyl acetate / 22.5 h

12: 85 percent / N-ethyldiisopropylamine / 4-dimethylaminopyridine / CH₂Cl₂ / 1.) 0 deg C, 40 min; 2.) rt,1.33 h

13: lithium diisopropylamide / hexane; tetrahydrofuran / 1.) 0 deg C, 50 min; 2.) rt, 50 min

14: 83 percent / n-BuLi / hexane; tetrahydrofuran / 1.1 h / Ambient temperature

15: pyridinium p-toluenesulfonate / dimethylformamide / 0.83 h / Ambient temperature

16: sodium hydride / dimethylformamide / 1.25 h

17: 99 percent / acetic acid; tetrahydrofuran; propan-2-ol / 8.5 h / Ambient temperature

18: 88 percent / dicyclohexylcarbodiimide, pyridine, trifluoroacetic acid, DMSO / benzene / 4.5 h / Ambient temperature

19: 61 percent / (1S)-(+)-10-camphorsulfonic acid / methanol; toluene / 3 h / Ambient temperature

20: 65 percent / ethanethiol, sodium hydride / dimethylformamide / 1 h / 150 °C

With pyridine; potassium hydroxide; sodium hydroxide; n-butyllithium; Amberlyst 15; hydroxylamine hydrochloride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; (+)-10-camphorsulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; ethanethiol; lithium diisopropyl amide; dmap; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; xylene; benzene;

DOI:10.1016/S0040-4020(01)83440-2

upstream raw materials:

4-[(phenylmethoxy)methyl]-2-cyclohex-2-en-1-one

acrylic acid methyl ester

Downstream raw materials:

(1R,2S,6S,7S)-2-Benzyloxymethyl-5,5-dimethoxy-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

2-((1R,2S,6S,7S)-2-Benzyloxymethyl-5,5-dimethoxy-bicyclo[4.2.0]oct-7-yl)-propan-2-ol

(1S,5S,6R,8S)-5-Benzyloxymethyl-3-[1-hydroxy-meth-(Z)-ylidene]-8-(1-methoxymethoxy-1-methyl-ethyl)-bicyclo[4.2.0]octan-2-one

C₃₁H₃₉NO₄