(3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one
• CAS No.: 158742-08-6
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• Mol file: 158742-08-6.mol

Synonyms:(3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one

Chemical Property of (3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one

There total 6 articles about (3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-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: 70.0%

(3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one (149706-06-9) → N-(4-Methoxyphenyl)-4-cyclohexyl-3-hydroxybutanamide + (3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one (158742-08-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 15h; under 760 Torr;

DOI:10.1021/jo00069a048

Reference yield:

(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone (149818-33-7) → (3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one (158742-08-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / aq. NaIO₄ / ethyl acetate / 4 h / 50 °C

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

3: 70 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 15 h / 760 Torr

With sodium periodate; n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate;

DOI:10.1021/jo00069a048

Reference yield:

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone (148968-08-5) → (3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one (158742-08-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 70 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 15 h / 760 Torr

With n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; hexane;

DOI:10.1021/jo00069a048

upstream raw materials:

(3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone

(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone

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

Downstream raw materials:

(3R,4S)-4-(Cyclohexylmethyl)-1-(4-methoxyphenyl)-3-triisopropylsilyloxy-2-azetidinone