(S)-N-(4-Fluorophenyl)-1-[hydroxy[4-(phenylmethoxy)phenyl]methyl]-4-oxo-cyclohexanecarboxamide

Base Information

• Chemical Name: (S)-N-(4-Fluorophenyl)-1-[hydroxy[4-(phenylmethoxy)phenyl]methyl]-4-oxo-cyclohexanecarboxamide
• CAS No.: 182227-24-3
• Molecular Formula: C₂₇H₂₆FNO₄
• Molecular Weight: 447.506
• DSSTox Substance ID: DTXSID60444901
• Wikidata: Q82263175
• Mol file: 182227-24-3.mol

Synonyms:182227-24-3;(S)-N-(4-Fluorophenyl)-1-[hydroxy[4-(phenylmethoxy)phenyl]methyl]-4-oxo-cyclohexanecarboxamide;N-(4-fluorophenyl)-1-[(S)-hydroxy-(4-phenylmethoxyphenyl)methyl]-4-oxocyclohexane-1-carboxamide;DTXSID60444901;BEDDNSKYSRIEEJ-VWLOTQADSA-N

Chemical Property of (S)-N-(4-Fluorophenyl)-1-[hydroxy[4-(phenylmethoxy)phenyl]methyl]-4-oxo-cyclohexanecarboxamide

Chemical Property:

• PSA: 75.63000
• LogP: 5.27930
• Solubility.: Dichloromethane, Ethyl Acetate, Tetrahydrofuran
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 447.18458647
• Heavy Atom Count: 33
• Complexity: 639

Purity/Quality:

(S)-N-(4-Fluorophenyl)-1-[hydroxy[4-(phenylmethoxy)phenyl]methyl]-4-oxo-cyclohexanecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CCC1=O)(C(C2=CC=C(C=C2)OCC3=CC=CC=C3)O)C(=O)NC4=CC=C(C=C4)F
• Isomeric SMILES: C1CC(CCC1=O)([C@H](C2=CC=C(C=C2)OCC3=CC=CC=C3)O)C(=O)NC4=CC=C(C=C4)F

Technology Process of (S)-N-(4-Fluorophenyl)-1-[hydroxy[4-(phenylmethoxy)phenyl]methyl]-4-oxo-cyclohexanecarboxamide

There total 5 articles about (S)-N-(4-Fluorophenyl)-1-[hydroxy[4-(phenylmethoxy)phenyl]methyl]-4-oxo-cyclohexanecarboxamide 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:

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (1489-97-0) → 1-[(S)-(4-Benzyloxy-phenyl)-hydroxy-methyl]-4-oxo-cyclohexanecarboxylic acid (4-fluoro-phenyl)-amide (182227-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C, 30 min, -20 deg C --> rt, 1 h

2: N-(2-naphthalenesulfonyl)-D-valine, BH₃*THF / various solvent(s) / 3 h / -78 °C

3: n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) Me₃Al / 1) CH₂Cl₂, toluene, rt, 30 min; 2) CH₂Cl₂, toluene. 50-55 deg C, 2 d

With borane-THF; tetrabutyl ammonium fluoride; trimethylaluminum; N-(2-naphthalenesulfonyl)-D-valine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo9704366

Reference yield:

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → 1-[(S)-(4-Benzyloxy-phenyl)-hydroxy-methyl]-4-oxo-cyclohexanecarboxylic acid (4-fluoro-phenyl)-amide (182227-24-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / 4-MeC₆H₄SO₃H / Heating

2: 1.) LDA / 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C, 30 min, -20 deg C --> rt, 1 h

3: N-(2-naphthalenesulfonyl)-D-valine, BH₃*THF / various solvent(s) / 3 h / -78 °C

4: n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

5: 1.) Me₃Al / 1) CH₂Cl₂, toluene, rt, 30 min; 2) CH₂Cl₂, toluene. 50-55 deg C, 2 d

With borane-THF; tetrabutyl ammonium fluoride; trimethylaluminum; toluene-4-sulfonic acid; N-(2-naphthalenesulfonyl)-D-valine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo9704366

Reference yield:

[(1,4-Dioxa-spiro[4.5]dec-8-ylidene)-ethoxy-methoxy]-trimethyl-silane (182227-16-3) → 1-[(S)-(4-Benzyloxy-phenyl)-hydroxy-methyl]-4-oxo-cyclohexanecarboxylic acid (4-fluoro-phenyl)-amide (182227-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-(2-naphthalenesulfonyl)-D-valine, BH₃*THF / various solvent(s) / 3 h / -78 °C

2: n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

3: 1.) Me₃Al / 1) CH₂Cl₂, toluene, rt, 30 min; 2) CH₂Cl₂, toluene. 50-55 deg C, 2 d

With borane-THF; tetrabutyl ammonium fluoride; trimethylaluminum; N-(2-naphthalenesulfonyl)-D-valine; In tetrahydrofuran;

DOI:10.1021/jo9704366

upstream raw materials:

4-fluoroaniline

8-[(S)-(4-Benzyloxy-phenyl)-hydroxy-methyl]-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate

ethyl 4-oxocyclohexane-1-carboxylate

Downstream raw materials:

(R)-3-(4-Benzyloxy-phenyl)-7-(4-chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-2-aza-spiro[3.5]nonan-1-one

(R)-7-(4-Chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-3-(4-hydroxy-phenyl)-2-aza-spiro[3.5]nonan-1-one

(+)-(R)-2-(4-fluorophenyl)-3-(4-(benzyloxy)phenyl)-2-azaspiro[3.5]nonane-1,7-dione

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