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

Base Information

Chemical Name:(1S,5R)-4,6-dioxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester
CAS No.:1037367-68-2
Molecular Formula:C₂₀H₂₅NO₄
Molecular Weight:343.423
Hs Code.:

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

There total 2 articles about (1S,5R)-4,6-dioxo-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: 6.5%

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

: 1037367-68-2
(1S,5R)-4,6-dioxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -69 ℃; for 1.5h; Inert atmosphere;
DOI:10.1248/cpb.c18-00671

Reference yield:

: C₂₀H₂₇NO₅

: 1037367-68-2
(1S,5R)-4,6-dioxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 72 h / 20 °C

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

With sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; N,N-dimethyl-formamide;
DOI:10.1248/cpb.c18-00671

Reference yield: 76.0%

: 1037367-68-2
(1S,5R)-4,6-dioxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

: 74-88-4
methyl iodide

: 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

Guidance literature:: (1S,5R)-4,6-dioxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h; Inert atmosphere; Cooling with ice;
DOI:10.1248/cpb.c18-00671