(4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

Base Information

• Chemical Name: (4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde
• CAS No.: 1383736-55-7
• Molecular Formula: C₁₆H₁₇NO₂
• Molecular Weight: 255.316
• Mol file: 1383736-55-7.mol

Synonyms:(4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

Chemical Property of (4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

There total 4 articles about (4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde 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: 85.0%

4-((4R,5R)-4-acetyl-5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)butanal (1383736-52-4) → (4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde (1383736-55-7)

Guidance literature:

With silica gel; N-ethyl-N,N-diisopropylamine; In toluene; at 75 ℃; for 48h;

DOI:10.1021/ol301461e

Reference yield:

(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate (1383736-53-5) → (4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde (1383736-55-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,O-dimethylhydroxylamine*hydrochloride / tetrahydrofuran / 0.08 h / Inert atmosphere

1.2: -5 - 20 °C / Inert atmosphere

2.1: ozone / ethyl acetate / -78 °C

2.2: 8 h / Inert atmosphere; Reflux

3.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

With N,O-dimethylhydroxylamine*hydrochloride; silica gel; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethyl acetate; toluene; 3.1: Aldol condensation;

DOI:10.1021/ol301461e

Reference yield:

1-((4R,5R)-5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazol-4-yl)ethanone (1383736-54-6) → (4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde (1383736-55-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ozone / ethyl acetate / -78 °C

1.2: 8 h / Inert atmosphere; Reflux

2.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

With silica gel; ozone; N-ethyl-N,N-diisopropylamine; In ethyl acetate; toluene; 2.1: Aldol condensation;

DOI:10.1021/ol301461e

upstream raw materials:

4-((4R,5R)-4-acetyl-5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)butanal

(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

1-((4R,5R)-5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazol-4-yl)ethanone

(4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

Downstream raw materials:

(4R,5S,7R)-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-yl benzoate

C₁₇H₂₂N₄O₅

(4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene

(4R,5S,7R)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene