<3R^*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole

Base Information

• Chemical Name: <3R^*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole
• CAS No.: 107770-21-8
• Molecular Formula: C₁₅H₁₉NO
• Molecular Weight: 229.322

Synonyms:

Chemical Property of <3R^*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3R^*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole

There total 22 articles about <3R^*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole 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:

benzyl bromide (100-39-0) + 3-Ethyl-4,5,6,6a-tetrahydro-3aH-cyclopentisoxazol (69423-37-6,73661-46-8) → <3R*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole (107770-21-8,107869-81-8)

Guidance literature:

With n-butyllithium; diethylamine; Yield given. Multistep reaction; 1.) THF, hexane, HMPA, -80 deg C, 2 h, 2.) THF, hexane, HMPA, -80 deg C, 1 h;

DOI:10.1021/ja00244a027

Reference yield:

benzaldehyde (100-52-7) → <3S*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole (107770-21-8,107869-81-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) LDA, hexamethylphosphoric triamide / 1) THF, -80 deg C, 20 h, 2) -80 deg C, 1 h

2: 1) LDEA, hexamethylphosphoric triamide / 1) THF, -78 deg C

4: Bu₃SnH, AIBN / benzene / 1 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium diisopropyl amide; In benzene;

DOI:10.1016/S0040-4020(01)89051-7

Reference yield:

(3aS,6aS)-3-Phenethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole (107770-45-6) + methyl iodide (74-88-4) → <3S*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole (107770-21-8,107869-81-8) + <3R*,4α,5α>-3a,5,6,6a-tetrahydro-3-(1-methyl-2-phenylethyl)-4H-cyclopentisoxazole (107770-21-8,107869-81-8)

Guidance literature:

With n-butyllithium; diethylamine; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, hexane, HMPA, -80 deg C, 2.) THF, hexane, HMPA, -80 deg C;

DOI:10.1021/ja00244a027

upstream raw materials:

Dithiocarbonic acid S-methyl ester O-((1S,2S)-1-phenyl-2-(3aS,6aS)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazol-3-yl-propyl) ester

Dithiocarbonic acid S-methyl ester O-((1R,2S)-1-phenyl-2-(3aS,6aS)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazol-3-yl-propyl) ester

(3aS,6aS)-3-Phenethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole

methyl iodide

Downstream raw materials:

<2R^*,1α,2α>-2-(2-methyl-3-phenyl-1-oxopropyl)cyclopentanol

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