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

Base Information

• Chemical Name: 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
• CAS No.: 464170-11-4
• Molecular Formula: C₄₇H₅₂N₂O₆
• Molecular Weight: 740.94
• Mol file: 464170-11-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 78.0%

tert-butyl (3S)-3-{6-(N-benzyl-N-isopropylamino)-2-(S)-hydroxy[4-methoxy-2-(4-methoxybenzyloxymethyl)phenyl]-methyl-3-pyridinyl}-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate (464170-10-3) → 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)

Guidance literature:

With sodium hexamethyldisilazane; diethyl chlorophosphate; In tetrahydrofuran; at -30 ℃; for 0.5h;

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

Reference yield:

2,6-dichloropyridine (2402-78-0) → 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)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / hexane; toluene / -64 - 0 °C

1.2: 99 percent / hexane; toluene / 4 - 20 °C

2.1: POCl₃ / 8 - 20 °C

2.2: 99 percent / toluene / 8 h / 70 °C

3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: ClPO(OEt)2 / tetrahydrofuran; hexane / -78 - 0 °C

3.3: tetrahydrofuran; hexane / 0.5 h / 0 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: tetrahydrofuran; hexane / 1 h / -78 °C

4.3: 60 percent / conc. H₂SO₄ / dioxane; H₂O / 1.5 h / 100 °C

5.1: EDC; 4-dimethylaminopyridine / tetrahydrofuran / 12 h / 20 °C

6.1: 87 percent / sodium acetate; Pd(OAc)2; DPPF / toluene / 18 h / 120 °C / 760 Torr

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 75 percent / tetrahydrofuran; hexane / 0.2 h / -78 °C

8.1: 66 percent / LS-selectride / tetrahydrofuran / 5 h / 0 °C

9.1: 78 percent / (EtO)2POCl; NaHMDS / tetrahydrofuran / 0.5 h / -30 °C

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; n-butyllithium; sodium acetate; sodium hexamethyldisilazane; diethyl chlorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; lithium tri-sec-butyl(hydrido)borate; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; hexane; toluene; 2.1: Vilsmeier formylation;

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

Reference yield:

Benzyl-isopropyl-amin (102-97-6) → 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)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / hexane; toluene / -64 - 0 °C

1.2: 99 percent / hexane; toluene / 4 - 20 °C

2.1: POCl₃ / 8 - 20 °C

2.2: 99 percent / toluene / 8 h / 70 °C

3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: ClPO(OEt)2 / tetrahydrofuran; hexane / -78 - 0 °C

3.3: tetrahydrofuran; hexane / 0.5 h / 0 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: tetrahydrofuran; hexane / 1 h / -78 °C

4.3: 60 percent / conc. H₂SO₄ / dioxane; H₂O / 1.5 h / 100 °C

5.1: EDC; 4-dimethylaminopyridine / tetrahydrofuran / 12 h / 20 °C

6.1: 87 percent / sodium acetate; Pd(OAc)2; DPPF / toluene / 18 h / 120 °C / 760 Torr

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 75 percent / tetrahydrofuran; hexane / 0.2 h / -78 °C

8.1: 66 percent / LS-selectride / tetrahydrofuran / 5 h / 0 °C

9.1: 78 percent / (EtO)2POCl; NaHMDS / tetrahydrofuran / 0.5 h / -30 °C

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; n-butyllithium; sodium acetate; sodium hexamethyldisilazane; diethyl chlorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; lithium tri-sec-butyl(hydrido)borate; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; hexane; toluene; 2.1: Vilsmeier formylation;

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

upstream raw materials:

tert-butyl (3S)-3-{6-(N-benzyl-N-isopropylamino)-2-(S)-hydroxy[4-methoxy-2-(4-methoxybenzyloxymethyl)phenyl]-methyl-3-pyridinyl}-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

2,6-dichloropyridine

Benzyl-isopropyl-amin

2-(N-benzylisopropylamino)-6-chloropyridine

Downstream raw materials:

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