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

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Chemical Name:(1S,5R)-5-fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester
CAS No.:1037367-51-3
Molecular Formula:C₂₀H₂₆FNO₃
Molecular Weight:347.43
Hs Code.:

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

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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 tert-butyl ester

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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 tert-butyl ester

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

: 1037367-50-2
(3S)-3-(3-phenylsulfonyloxy-1-propyl)-4-fluoro-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

: 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

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -15 - 0 ℃; for 1.5h;

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

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

Guidance literature:: Multi-step reaction with 3 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

With dmap; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; acetic acid; triethylamine; 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

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

Guidance literature:: Multi-step reaction with 4 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

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