(1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

Base Information

Chemical Name:(1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid
CAS No.:1037367-53-5
Molecular Formula:C₁₆H₁₈FNO₃
Molecular Weight:291.322
Hs Code.:

Synonyms:(1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

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Chemical Property of (1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

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Technology Process of (1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

There total 5 articles about (1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid 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:

: 1037367-51-3
(1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

: 1037367-53-5
(1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 6h;

Reference yield:

: 1037367-48-8
(3S)-3-[3-(tert-butyldimethylsilyloxy)-1-propyl]- 4-fluoro-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

: 1037367-53-5
(1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 21.5 h / 20 °C / Cooling with ice

2: triethylamine; dmap / dichloromethane / 12.5 h / 20 °C / Cooling with ice

3: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.5 h / -15 - 0 °C / Inert atmosphere

4: trifluoroacetic acid / dichloromethane / 6 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1248/cpb.c18-00671

Reference yield:

: 1037367-47-7
(3S)-3-[3-(tert-butyldimethylsilyloxy)-1-propyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

: 1037367-53-5
(1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -15 - -5 °C / Inert atmosphere

1.2: 17 h / -15 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 21.5 h / 20 °C / Cooling with ice

3.1: triethylamine; dmap / dichloromethane / 12.5 h / 20 °C / Cooling with ice

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.5 h / -15 - 0 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; acetic acid; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1248/cpb.c18-00671