5H-Cyclopenta[b]pyridine-6-carboxylic acid, 5-(2,3-dihydro-6-benzofuranyl)-6,7-dihydro-7-[2-(hydroxymethyl)-4-meth oxyphenyl]-2-[(1-methylethyl)amino]-, 1,1-dimethylethyl ester, (5S,6R,7R)-

Base Information

• Chemical Name: 5H-Cyclopenta[b]pyridine-6-carboxylic acid, 5-(2,3-dihydro-6-benzofuranyl)-6,7-dihydro-7-[2-(hydroxymethyl)-4-meth oxyphenyl]-2-[(1-methylethyl)amino]-, 1,1-dimethylethyl ester, (5S,6R,7R)-
• CAS No.: 494841-92-8
• Molecular Formula: C32H38N2O5
• Molecular Weight: 530.664
• Mol file: 494841-92-8.mol

Synonyms:

Chemical Property of 5H-Cyclopenta[b]pyridine-6-carboxylic acid, 5-(2,3-dihydro-6-benzofuranyl)-6,7-dihydro-7-[2-(hydroxymethyl)-4-meth oxyphenyl]-2-[(1-methylethyl)amino]-, 1,1-dimethylethyl ester, (5S,6R,7R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5H-Cyclopenta[b]pyridine-6-carboxylic acid, 5-(2,3-dihydro-6-benzofuranyl)-6,7-dihydro-7-[2-(hydroxymethyl)-4-meth oxyphenyl]-2-[(1-methylethyl)amino]-, 1,1-dimethylethyl ester, (5S,6R,7R)-

There total 26 articles about 5H-Cyclopenta[b]pyridine-6-carboxylic acid, 5-(2,3-dihydro-6-benzofuranyl)-6,7-dihydro-7-[2-(hydroxymethyl)-4-meth oxyphenyl]-2-[(1-methylethyl)amino]-, 1,1-dimethylethyl ester, (5S,6R,7R)- 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:

tert-butyl (5S,6R,7R)-2-(N-benzyl-N-isopropylamino)-5-(2,3-dihydro-1-benzofuran-6-yl)-7-[4-methoxy-2-(4-methoxybenzyloxymethyl)phenyl]-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate (464170-11-4) → tert-butyl (5S,6R,7R)-(+)-5-(2,3-dihydrobenzo[b]furan-6-yl)-7-(2-hydroxymethyl-4-methoxyphenyl)-2-(N-isopropylamino)-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate (494841-92-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; at 20 ℃; for 20h; under 760 Torr;

DOI:10.1016/S0040-4020(02)00280-6

Reference yield:

5-bromo-2,2-difluoro-2H-1,3-benzodioxole (33070-32-5) → tert-butyl (5S,6R,7R)-(+)-5-(2,3-dihydrobenzo[b]furan-6-yl)-7-(2-hydroxymethyl-4-methoxyphenyl)-2-(N-isopropylamino)-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate (494841-92-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Mg / tetrahydrofuran

1.2: tetrahydrofuran / -78 °C

2.1: 4-(dimethylamino)pyridine / CHCl₃ / 20 °C

3.1: H₂; NaHCO₃ / Pd(OH)2/C / tetrahydrofuran; ethanol / 20 °C / 760 Torr

4.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C

5.1: 4-(dimethylamino)pyridine / CHCl₃ / 0 °C

6.1: PdCl₂(PPh₃)2; NaHCO₃ / dimethylformamide / 130 °C

7.1: NaBH₄ / methanol / 20 °C

8.1: 4-(dimethylamino)pyridine / tetrahydrofuran / 20 °C

9.1: m-CPBA / CHCl₃ / 0 °C

10.1: 32.2 g / triethylamine / CHCl₃ / Heating

11.1: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 2 h / -78 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; chloroform; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.2: Grignard reaction / 6.1: Heck reaction;

DOI:10.1016/j.bmc.2004.02.033

Reference yield:

7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine (496047-46-2) → tert-butyl (5S,6R,7R)-(+)-5-(2,3-dihydrobenzo[b]furan-6-yl)-7-(2-hydroxymethyl-4-methoxyphenyl)-2-(N-isopropylamino)-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate (494841-92-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Mg / tetrahydrofuran

1.2: tetrahydrofuran / -78 °C

2.1: 4-(dimethylamino)pyridine / CHCl₃ / 20 °C

3.1: H₂; NaHCO₃ / Pd(OH)2/C / tetrahydrofuran; ethanol / 20 °C / 760 Torr

4.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C

5.1: 4-(dimethylamino)pyridine / CHCl₃ / 0 °C

6.1: PdCl₂(PPh₃)2; NaHCO₃ / dimethylformamide / 130 °C

7.1: NaBH₄ / methanol / 20 °C

8.1: 4-(dimethylamino)pyridine / tetrahydrofuran / 20 °C

9.1: m-CPBA / CHCl₃ / 0 °C

10.1: 32.2 g / triethylamine / CHCl₃ / Heating

11.1: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 2 h / -78 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; chloroform; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.2: Grignard reaction / 6.1: Heck reaction;

DOI:10.1016/j.bmc.2004.02.033

upstream raw materials:

tert-butyl (5S,6R,7R)-2-(N-benzyl-N-isopropylamino)-5-(2,3-dihydro-1-benzofuran-6-yl)-7-[4-methoxy-2-(4-methoxybenzyloxymethyl)phenyl]-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

5-bromo-2,2-difluoro-2H-1,3-benzodioxole

7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine

5-(2,3-dihydro-benzofuran-6-yl)-7-[4-methoxy-2-(4-methoxy-benzyloxymethyl)-phenyl]-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester