benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

Base Information

Chemical Name:benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate
CAS No.:1005181-17-8
Molecular Formula:C₂₂H₃₄N₄O₃
Molecular Weight:402.537
Hs Code.:

Synonyms:benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

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Chemical Property of benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

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Technology Process of benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

There total 4 articles about benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate 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: 94.5%

: 1005181-14-5
2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexylcarbamate

: 1005181-17-8
benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

Guidance literature:: 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexylcarbamate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

With sodium hydrogencarbonate; In dichloromethane; water;

Reference yield:

: tert-butyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexylcarbamate

: 1005181-17-8
benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

Guidance literature:: With methanesulfonic acid; In isopropyl alcohol; toluene; at 55 - 65 ℃; for 2h; Inert atmosphere; Large scale;
DOI:10.1021/acs.oprd.6b00282

Reference yield:

: C₂₅H₃₇N₃O₅

: 1005181-17-8
benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrogenchloride / water / 20 h / 58 - 63 °C / Large scale

1.2: 17 - 25 °C / Inert atmosphere; Large scale

2.1: diphenyl hydrogen phosphate / tert-butyl alcohol; toluene / 90 - 92 °C / Inert atmosphere; Large scale

2.2: 2.25 h / 75 - 82 °C / Inert atmosphere; Large scale

2.3: Large scale

3.1: methanesulfonic acid / toluene; isopropyl alcohol / 2 h / 55 - 65 °C / Inert atmosphere; Large scale

With hydrogenchloride; diphenyl hydrogen phosphate; methanesulfonic acid; In water; isopropyl alcohol; toluene; tert-butyl alcohol; 2.1: |Curtius Rearrangement / 2.2: |Curtius Rearrangement;
DOI:10.1021/acs.oprd.6b00282