4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl ester

Base Information

• Chemical Name: 4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl ester
• CAS No.: 126107-18-4
• Molecular Formula: C₂₄H₃₁BrO₆
• Molecular Weight: 495.411
• Mol file: 126107-18-4.mol

Synonyms:4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl ester

Chemical Property of 4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl ester

There total 16 articles about 4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl 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:

methyl 1-methyl-2-oxocyclopentane-1-carboxylate (30680-84-3) → 4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl ester (126107-18-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) sodium hydride / 1) THF, r.t., 1 h, 2) THF, 15 h

2: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 24 h / Ambient temperature

3: 57 percent / BH₃*THF / tetrahydrofuran / 20 h / Ambient temperature

4: 87 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

5: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

6: 93 percent / H₂ / 3(py)>PF₆ / CH₂Cl₂ / 3 h / Ambient temperature

7: 91 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

8: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

9: 66 percent / NH₃, lithium / diethyl ether / 1.5 h / Heating

10: 75 percent / silver carbonate on Celite, / benzene / 14 h / Heating

11: 90 percent / potassium carbonate, H₂ / 5percent Rh/C / ethyl acetate / 14 h

12: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

13: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

With 1H-imidazole; dmap; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; tetrabutyl ammonium fluoride; ammonia; hydrogen; tert.-butyl lithium; lithium; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic acid; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; Rh on carbon; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00297a024

Reference yield:

3-ethoxycyclopent-2-en-1-one (22627-70-9) → 4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl ester (126107-18-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 15 min, 2) THF, -78 deg C, 45 min

2: 86 percent / pyridine, pyridinium bromide perbromide / CH₂Cl₂ / 14 h / 3 °C

3: 19.00 g / cerium(III) chloride heptahydrate, sodium borohydride / methanol / 0.33 h

4: diisopropylethylamine / CH₂Cl₂ / 20 h / Ambient temperature

5: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

6: 66 percent / NH₃, lithium / diethyl ether / 1.5 h / Heating

7: 75 percent / silver carbonate on Celite, / benzene / 14 h / Heating

8: 90 percent / potassium carbonate, H₂ / 5percent Rh/C / ethyl acetate / 14 h

9: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

10: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; ammonia; hydrogen; tert.-butyl lithium; pyridinium hydrobromide perbromide; lithium; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; silver carbonate; Rh on carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/jo00297a024

Reference yield:

3-Benzyloxymethyl-2-bromo-cyclopent-2-enol (126019-77-0) → 4-Bromo-benzoic acid 2-[(1S,2R)-2-((1R,3aS,6S,6aS)-6-methoxymethoxy-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-2-methyl-cyclopentyl]-ethyl ester (126107-18-4)

Guidance literature:

Multi-step reaction with 7 steps

1: diisopropylethylamine / CH₂Cl₂ / 20 h / Ambient temperature

2: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

3: 66 percent / NH₃, lithium / diethyl ether / 1.5 h / Heating

4: 75 percent / silver carbonate on Celite, / benzene / 14 h / Heating

5: 90 percent / potassium carbonate, H₂ / 5percent Rh/C / ethyl acetate / 14 h

6: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

7: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

With dmap; tetrabutyl ammonium fluoride; ammonia; hydrogen; tert.-butyl lithium; lithium; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; silver carbonate; Rh on carbon; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/jo00297a024

upstream raw materials:

3-ethoxycyclopent-2-en-1-one

methyl 1-methyl-2-oxocyclopentane-1-carboxylate

methyl (E)-(2-hydroxyethylidene)-1-methylcyclopentanecarboxylate

3-Benzyloxymethyl-2-bromo-cyclopent-2-enol