(4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

Base Information

• Chemical Name: (4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate
• CAS No.: 474827-09-3
• Molecular Formula: C₂₁H₂₃N₃O₅
• Molecular Weight: 397.431
• Mol file: 474827-09-3.mol

Synonyms:(4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

Chemical Property of (4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

There total 7 articles about (4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate 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: 76.0%

(2E)-5-(4-methoxybenzyloxy)-2-pentenoic acid (292850-52-3) + (4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-ol → (4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate (474827-09-3)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1002/1099-0690(200206)2002:12<1941::AID-EJOC1941>3.0.CO;2-T

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate (474827-09-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / pTsOH*H₂O / toluene / 11 h / 110 °C

2: 91 percent / DIBAL / toluene / 20 °C

3: DMSO; oxalyl chloride; TEA / CH₂Cl₂

4: 98 percent / K₂CO₃ / H₂O / 20 °C

5: 72 percent / NaOH / tetrahydrofuran; H₂O / 5 h / 20 °C

6: 76 percent / DMAP; 1,3-diisopropylcarbodiimide / tetrahydrofuran / 24 h / 20 °C

With dmap; sodium hydroxide; oxalyl dichloride; TEA; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; diisopropyl-carbodiimide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; toluene; 3: Swern oxidation / 4: Horner-Wadsworth-Emmons reaction;

DOI:10.1002/1099-0690(200206)2002:12<1941::AID-EJOC1941>3.0.CO;2-T

Reference yield:

4-(tetrahydro-pyran-2-yloxy)-hexahydro-pyrrolo[1,2-b]isoxazole-2,3-dicarbonitrile → (4S)-2,3-dicyanohexahydropyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate (474827-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Amberlyst 15(R) / methanol / 1 h / 55 °C

2: 76 percent / DMAP; 1,3-diisopropylcarbodiimide / tetrahydrofuran / 24 h / 20 °C

With dmap; diisopropyl-carbodiimide; Amberlyst 15(R); In tetrahydrofuran; methanol;

DOI:10.1002/1099-0690(200206)2002:12<1941::AID-EJOC1941>3.0.CO;2-T

upstream raw materials:

(2E)-5-(4-methoxybenzyloxy)-2-pentenoic acid

2-(4-methoxy-phenyl)-[1,3]dioxane

3-(p-methoxybenzyloxy)propanal

4-methoxy-benzaldehyde

Downstream raw materials:

(+)-(2aS,3R,6aS,6bS)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one