1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

Base Information

• Chemical Name: 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane
• CAS No.: 335160-93-5
• Molecular Formula: C₂₇H₂₈FN₅O₃
• Molecular Weight: 489.549
• Mol file: 335160-93-5.mol

Synonyms:1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

Chemical Property of 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

There total 10 articles about 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane 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: 56.0%

(1S,5S)-1-Benzyl-3-(2,4-dimethoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one; hydrochloride + 2-fluoro-4-[(5-formyl-1H-imidazol-1-yl)methyl]benzonitrile (254108-49-1) → 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane (335160-93-5)

Guidance literature:

With 4 A molecular sieve; sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; for 24h;

DOI:10.1021/ol015504w

Reference yield:

5(S)-5-allyl-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-2-piperazinone → 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane (335160-93-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2.5 h

1.2: NaIO₄; NaHCO₃ / H₂O; 2-methyl-propan-2-ol; tetrahydrofuran / 2 h

2.1: 70 percent / NaBH₄ / ethanol / 0.33 h / 0 °C

3.1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

4.1: 63 percent / LDA / tetrahydrofuran / -78 - 0 °C

5.1: 100 percent / HCl / ethyl acetate / 0.38 h / 0 °C

6.1: 56 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 24 h

With hydrogenchloride; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; sodium tris(acetoxy)borohydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; tert-butyl alcohol;

DOI:10.1021/ol015504w

Reference yield:

2,4-dimethoxybenzylamine hydrochloride (20781-21-9) → 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane (335160-93-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 90 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 14 h / 20 °C

2.1: 93 percent / NaHCO₃ / ethyl acetate; H₂O / 0.33 h / 0 °C

3.1: 75 percent / Cs₂CO₃ / dimethylformamide / 2 h / 65 °C

4.1: LiHMDS / tetrahydrofuran / 3.5 h / -78 °C

5.1: OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2.5 h

5.2: NaIO₄; NaHCO₃ / H₂O; 2-methyl-propan-2-ol; tetrahydrofuran / 2 h

6.1: 70 percent / NaBH₄ / ethanol / 0.33 h / 0 °C

7.1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

8.1: 63 percent / LDA / tetrahydrofuran / -78 - 0 °C

9.1: 100 percent / HCl / ethyl acetate / 0.38 h / 0 °C

10.1: 56 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 24 h

With hydrogenchloride; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; caesium carbonate; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ol015504w

upstream raw materials:

2-fluoro-4-[(5-formyl-1H-imidazol-1-yl)methyl]benzonitrile

2,4-dimethoxybenzylamine hydrochloride

(1S)-tert-butyl-1-{[(2,4-dimethoxybenzyl)amino]methyl}but-3-enylcarbamate

(S)-5-allyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-2-piperazinone

Downstream raw materials:

1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane