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

Base Information

Chemical Name:(1S,5S)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester
CAS No.:1037367-85-3
Molecular Formula:C₁₈H₂₃NO₃
Molecular Weight:301.386
Hs Code.:

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

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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 methyl ester

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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 methyl ester

There total 6 articles about (1S,5S)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl 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: 65.0%

: 1037367-83-1
(1S,5S)-6,6-ethanediyldimercapto-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester

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

Guidance literature:: With Raney nickel; In ethanol; for 5.5h; Reflux;
DOI:10.1248/cpb.c18-00671

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

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

Guidance literature:: Multi-step reaction with 3 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

With methanol; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; 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

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

Guidance literature:: Multi-step reaction with 5 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

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