(2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one

Base Information

• Chemical Name: (2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one
• CAS No.: 1440869-63-5
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Mol file: 1440869-63-5.mol

Synonyms:

Chemical Property of (2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one

There total 9 articles about (2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-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: 73.0%

C22H20F5NO4 → (2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one (1440869-63-5)

Guidance literature:

In water; acetonitrile; for 5h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201207800

Reference yield:

[(2S,4S,5S)-5-allyl-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol → (2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one (1440869-63-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 2-iodoxybenzoic acid / dichloromethane / 3 h / Inert atmosphere; Molecular sieve; Reflux

2: ozone / dichloromethane; methanol / 0.17 h / -78 °C / Inert atmosphere

3: sodium tetrahydroborate / dichloromethane; methanol / 2 h / -78 - 0 °C / Inert atmosphere

4: sodium tetrahydroborate; nickel dichloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere

5: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / toluene / 6 h / 0 - 80 °C / Inert atmosphere

6: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 4 h / 20 °C / Inert atmosphere

7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

8: tributylphosphine / toluene / 2 h / 80 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; lithium hydroxide monohydrate; 2-iodoxybenzoic acid; tributylphosphine; diphenylphosphoranyl azide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 8: |Aza-Wittig Reaction;

DOI:10.1002/anie.201207800

Reference yield:

(E)-methyl 3-[(2S,4R,5S)-5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acrylate → (2S,4aS,10aR)-2-(4-methoxyphenyl)hexahydro-4H-[1,3]dioxino[5,4-d]azocin-8(9H)-one (1440869-63-5)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium tetrahydroborate; nickel dichloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / toluene / 6 h / 0 - 80 °C / Inert atmosphere

3: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 4 h / 20 °C / Inert atmosphere

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

5: tributylphosphine / toluene / 2 h / 80 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; lithium hydroxide monohydrate; tributylphosphine; diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 5: |Aza-Wittig Reaction;

DOI:10.1002/anie.201207800

Downstream raw materials:

(5R,6S)-6-[(tert-butyldiphenylsilyloxy)methyl]-5-hydroxyazocan-2-one

(7S)-7-[(tert-butyldiphenylsilyloxy)methyl]-7a-hydroxytetrahydro-1H-pyrrolizin-3(2H)-one

[(1S)-7a-hydroxy-5-oxohexahydro-1H-pyrrolizin-1-yl]methyl benzoate

(1R,6R,7aS)-allyl-7a-hydroxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-oxo-6-(phenylthio)hexahydro-1H-pyrrolizine-1-carboxylate