(S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one
• CAS No.: 123731-37-3
• Molecular Formula: C₃₀H₃₅NO₅
• Molecular Weight: 489.612
• Mol file: 123731-37-3.mol

Synonyms:(S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one

There total 12 articles about (S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one 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: 52.0%

(S)-4-Benzyl-3-[(2E,7E,9E)-13-(4-methoxy-phenoxy)-trideca-2,7,9-trienoyl]-oxazolidin-2-one (123731-36-2) → (S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one (123731-37-3)

Guidance literature:

With dimethylaluminum chloride; In dichloromethane; at -30 ℃; for 5h;

DOI:10.1016/S0040-4039(00)99589-3

Reference yield:

4-(4-methoxyphenoxyl)butyraldehyde (201486-63-7) → (S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one (123731-37-3)

Guidance literature:

Multi-step reaction with 10 steps

1: LHMDS / tetrahydrofuran / 12 h / -40 - 20 °C

2: diisobutylalumnum hydride / diethyl ether / 1 h / -78 °C

3: pyridine / 14 h / Ambient temperature

4: 74 percent / Li₂CuCl₄ / 2 h / -30 °C

5: AcOH / H₂O; tetrahydrofuran / 4 h / 80 °C

6: t-BuOK / tetrahydrofuran / 5 h / -20 °C

7: 57 percent / 10percent NaOH / methanol; tetrahydrofuran / 10 h / Ambient temperature

8: (COCl)2 / toluene / 20 h / Ambient temperature

9: n-BuLi / tetrahydrofuran / 1.5 h / -78 °C

10: 52 percent / 1.3 eq. Me₂AlCl / CH₂Cl₂ / 5 h / -30 °C

With pyridine; sodium hydroxide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; dimethylaluminum chloride; diisobutylaluminium hydride; acetic acid; lithium hexamethyldisilazane; dilithium tetrachlorocuprate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;

DOI:10.1016/S0040-4039(00)99589-3

Reference yield:

4-(4-methoxybenzyloxy)butan-1-ol (123731-28-2) → (S)-4-Benzyl-3-{(3aS,4S,5S,7aR)-5-[3-(4-methoxy-phenoxy)-propyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl}-oxazolidin-2-one (123731-37-3)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridinium chlorochromate, MS₃A / CH₂Cl₂ / 0.25 h / Ambient temperature

2: LHMDS / tetrahydrofuran / 12 h / -40 - 20 °C

3: diisobutylalumnum hydride / diethyl ether / 1 h / -78 °C

4: pyridine / 14 h / Ambient temperature

5: 74 percent / Li₂CuCl₄ / 2 h / -30 °C

6: AcOH / H₂O; tetrahydrofuran / 4 h / 80 °C

7: t-BuOK / tetrahydrofuran / 5 h / -20 °C

8: 57 percent / 10percent NaOH / methanol; tetrahydrofuran / 10 h / Ambient temperature

9: (COCl)2 / toluene / 20 h / Ambient temperature

10: n-BuLi / tetrahydrofuran / 1.5 h / -78 °C

11: 52 percent / 1.3 eq. Me₂AlCl / CH₂Cl₂ / 5 h / -30 °C

With pyridine; sodium hydroxide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; dimethylaluminum chloride; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate; lithium hexamethyldisilazane; dilithium tetrachlorocuprate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;

DOI:10.1016/S0040-4039(00)99589-3

upstream raw materials:

(S)-4-Benzyl-3-[(2E,7E,9E)-13-(4-methoxy-phenoxy)-trideca-2,7,9-trienoyl]-oxazolidin-2-one

4-(4-methoxyphenoxyl)butyraldehyde

4-(4-methoxybenzyloxy)butan-1-ol

(2E,4E)-8-(4-Methoxy-phenoxy)-octa-2,4-dienoic acid ethyl ester

Downstream raw materials:

(S)-4-Benzyl-3-[(3aS,4S,5S,7aR)-5-(3-hydroxy-propyl)-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbonyl]-oxazolidin-2-one