(3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one

Base Information

• Chemical Name: (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one
• CAS No.: 1229616-22-1
• Molecular Formula: C₁₈H₁₇NO₂
• Molecular Weight: 279.338
• Mol file: 1229616-22-1.mol

Synonyms:(3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one

Chemical Property of (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one

There total 5 articles about (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-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: 79.0%

2-[2-(1,3-dioxolan-2-yl)ethyl]-N-[(1R)-2-hydroxy-1-phenylethyl]benzamide (1229616-17-4) → (3R,11aS)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo[3,2-b][2]benzazepin-5-(10H)-one (1229616-23-2) + (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one (1229616-22-1)

Guidance literature:

With hydrogenchloride; In chloroform; at 20 ℃; stereoselective reaction;

DOI:10.1016/j.tetasy.2010.03.019

Reference yield:

1-Bromo-2-iodobenzene (583-55-1) → (3R,11aS)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo[3,2-b][2]benzazepin-5-(10H)-one (1229616-23-2) + (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one (1229616-22-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydrogencarbonate; palladium diacetate; N-benzyl-N,N,N-triethylammonium chloride / N,N-dimethyl-formamide / 5.5 h / 45 °C

2.1: chloroform / Reflux

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -80 °C / Inert atmosphere

3.2: 1.25 h / Inert atmosphere

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / Inert atmosphere

4.2: 20.25 h / 20 °C / Inert atmosphere; Reflux

5.1: hydrogenchloride / water; chloroform / 16 h / 20 °C

With hydrogenchloride; n-butyllithium; N-benzyl-N,N,N-triethylammonium chloride; palladium diacetate; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1039/c5ob00731c

Reference yield:

3-(o-bromophenyl)propanal (107408-16-2) → (3R,11aS)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo[3,2-b][2]benzazepin-5-(10H)-one (1229616-23-2) + (3R,11aR)-3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo-[3,2-b][2]benzazepin-5(10H)-one (1229616-22-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: chloroform / Reflux

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -80 °C / Inert atmosphere

2.2: 1.25 h / Inert atmosphere

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / Inert atmosphere

3.2: 20.25 h / 20 °C / Inert atmosphere; Reflux

4.1: hydrogenchloride / water; chloroform / 16 h / 20 °C

With hydrogenchloride; n-butyllithium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; hexane; dichloromethane; chloroform; water;

DOI:10.1039/c5ob00731c

upstream raw materials:

2-[2-(1,3-dioxolan-2-yl)ethyl]-N-[(1R)-2-hydroxy-1-phenylethyl]benzamide

1-Bromo-2-iodobenzene

2-[2-(2-bromophenyl)ethyl]-1,3-dioxolane

2-[2-(1,3-dioxolan-2-yl)ethyl]benzoic acid

Downstream raw materials:

(3S)-2-[(1R)-2-hydroxy-1-phenylethyl]-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-2-benzazepin-1-one

(2R)-2-phenyl-2-[(3S)-3-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-2-benzazepin-2-yl]ethanol