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

Base Information

Chemical Name:(1S,5S)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid
CAS No.:1043880-40-5
Molecular Formula:C₁₇H₂₁NO₃
Molecular Weight:287.359
Hs Code.:

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

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

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

There total 7 articles about (1S,5S)-5-methyl-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:

: 1037367-85-3
(1S,5S)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester

: 1043880-40-5
(1S,5S)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

Guidance literature:: (1S,5S)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester; With methanol; sodium hydroxide; water; at 0 - 50 ℃; for 30h;

With hydrogenchloride; water; In methanol;

Reference yield:

: 1037367-82-0
(1S,5R)-5-methyl-4,6-dioxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

: 1043880-40-5
(1S,5S)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / toluene / 9 h / Reflux

2: methanol / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

3: Raney nickel / ethanol / 5.5 h / Reflux

4: sodium hydroxide / methanol; water / 30 h / 20 - 50 °C / Cooling with ice

With methanol; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; water; toluene;
DOI:10.1248/cpb.c18-00671

Reference yield:

: 1037367-67-1
(3S)-3-(2-methoxycarbonyl-1-ethyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

: 1043880-40-5
(1S,5S)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1.5 h / -69 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

2.2: 2.5 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: toluene-4-sulfonic acid / toluene / 9 h / Reflux

4.1: methanol / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

5.1: Raney nickel / ethanol / 5.5 h / Reflux

6.1: sodium hydroxide / methanol; water / 30 h / 20 - 50 °C / Cooling with ice

With methanol; sodium hydride; toluene-4-sulfonic acid; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; n-heptane; ethylbenzene; water; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.c18-00671