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

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Chemical Name:(3aR,4S)-hexahydro-2-phenylpyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate
CAS No.:474827-06-0
Molecular Formula:C₂₅H₂₉NO₅
Molecular Weight:423.509
Hs Code.:

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

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

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

There total 6 articles about (3aR,4S)-hexahydro-2-phenylpyrrolo[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: 70.0%

: 292850-56-7
(3aR,4S)-4-hydroxy-2-phenyl-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b]isoxazole

: 292850-52-3
(2E)-5-(4-methoxybenzyloxy)-2-pentenoic acid

: 474827-06-0
(3aR,4S)-hexahydro-2-phenylpyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

Guidance literature:: With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1002/1099-0690(200206)2002:12<1941::AID-EJOC1941>3.0.CO;2-T

Reference yield:

: 123-11-5
4-methoxy-benzaldehyde

: 474827-06-0
(3aR,4S)-hexahydro-2-phenylpyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

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: 70 percent / 1,3-diisopropylcarbodiimide; DMAP / CH₂Cl₂ / 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:

: 5689-71-4
2-(4-methoxy-phenyl)-[1,3]dioxane

: 474827-06-0
(3aR,4S)-hexahydro-2-phenylpyrrolo[1,2-b]isoxazol-4-yl (2E)-5-(4-methoxybenzyloxy)-2-pentenoate

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / DIBAL / toluene / 20 °C

2: DMSO; oxalyl chloride; TEA / CH₂Cl₂

3: 98 percent / K₂CO₃ / H₂O / 20 °C

4: 72 percent / NaOH / tetrahydrofuran; H₂O / 5 h / 20 °C

5: 70 percent / 1,3-diisopropylcarbodiimide; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium hydroxide; oxalyl dichloride; TEA; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; diisopropyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene; 2: Swern oxidation / 3: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1099-0690(200206)2002:12<1941::AID-EJOC1941>3.0.CO;2-T