[(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

Base Information

• Chemical Name: [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine
• CAS No.: 141781-23-9
• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.348
• Mol file: 141781-23-9.mol

Synonyms:[(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

Chemical Property of [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

There total 1 articles about [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine 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:

(R)-2,3-cyclohexylideneglyceraldehyde (78008-36-3) + 4-methoxy-aniline (104-94-9) → [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine (141781-23-9)

Guidance literature:

DOI:10.1016/S0040-4039(00)91874-4

Reference yield: 75.0%

Thioisobutyric acid S-pyridin-2-yl ester (81357-56-4) + [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine (141781-23-9) → 1-(4-methoxyphenyl)-3,3-dimethyl-4-(1,4-dioxaspiro<4.5>dec-2-yl)azetidin-2-one

Guidance literature:

With tin(IV) chloride; triethylamine; In dichloromethane; 1.) -78 deg C, 30 min; 2.) -78 deg C then RT;

DOI:10.1016/S0040-4020(01)85649-0

Reference yield:

[(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine (141781-23-9) → (3R,4S)-4-(Cyclohexylmethyl)-1-(4-methoxyphenyl)-3-triisopropylsilyloxy-2-azetidinone (144465-85-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) TiCl₄, TEA / 1.) CH₂Cl₂, -78 deg C, 30 min., 2.) CH₂Cl₂, 0 deg C, 5 h

2: TFA / H₂O / Ambient temperature

3: 100 percent / aq. NaIO₄ / ethyl acetate / 4 h / 50 °C

4: n-BuLi / hexane; tetrahydrofuran / Ambient temperature

5: 70 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 15 h / 760 Torr

6: imidazole / dimethylformamide / 15 h / Ambient temperature

With 1H-imidazole; sodium periodate; n-butyllithium; TEA; hydrogen; titanium tetrachloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; hexane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00069a048

upstream raw materials:

(R)-2,3-cyclohexylideneglyceraldehyde

4-methoxy-aniline

Downstream raw materials:

(S)-4-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-1-(4-methoxy-phenyl)-azetidin-2-one

(R)-4-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-1-(4-methoxy-phenyl)-azetidin-2-one

1-(4-methoxyphenyl)-4-(1,4-dioxaspiro<4.5>dec-2-yl)azetidin-2-one

(3S,4R)-3-Benzyloxy-4-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-1-(4-methoxy-phenyl)-azetidin-2-one