(2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine

Base Information

• Chemical Name: (2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine
• CAS No.: 636592-82-0
• Molecular Formula: C₂₂H₃₁NO₂
• Molecular Weight: 341.494

Synonyms:(2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine

Chemical Property of (2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine

Chemical Property:

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Technology Process of (2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine

There total 2 articles about (2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine 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:

(2S,4aS,7R,8aR)-2-hydroxymethyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine (636592-72-8) → (2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine (636592-82-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 1h;

DOI:10.1055/s-2003-40193

Reference yield:

(E)-1-(3-bromo-2-methylprop-1-en-1-yl)benzene (83126-01-6) → (2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine (636592-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / acetonitrile / Heating

2: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

With oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; In dichloromethane; acetonitrile; 2: Swern oxidation;

DOI:10.1055/s-2003-40193

Reference yield: 90.0%

N-methylhydroxyamine hydrochloride (4229-44-1) + (2S,4aS,7R,8aR)-2-formyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine (636592-82-0) → (1S,3aR,3bS,4aR,6R,8aS,10aR)-3,6,9,9,10a-Pentamethyl-1-phenyl-decahydro-2,4-dioxa-3,9a-diaza-pentaleno[1,2-b]naphthalene

Guidance literature:

With pyridine; In toluene; at 90 ℃; for 1.33333h;

DOI:10.1002/ejoc.200600242

upstream raw materials:

(2S,4aS,7R,8aR)-2-hydroxymethyl-4,4,7-trimethyl-N-(2-methyl-3-phenylallyl)octahydro-1,3-benzoxazine

(E)-1-(3-bromo-2-methylprop-1-en-1-yl)benzene

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