benzyl (S)-1-((1S,2R,4R)-2-formamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate → N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)formamide

HRID 2246590Notes

Reaction equation

HRID 2246590 reaction equation
[CH:1]([NH:3][C@@H:4]1[CH2:9][C@H:8]([N:10]([CH:12]([CH3:14])[CH3:13])[CH3:11])[CH2:7][CH2:6][C@@H:5]1[N:15]1[CH2:19][CH2:18][C@H:17]([NH:20]C(=O)OCC2C=CC=CC=2)[C:16]1=[O:31])=[O:2]>CO.[Pd]>[NH2:20][C@H:17]1[CH2:18][CH2:19][N:15]([C@H:5]2[CH2:6][CH2:7][C@@H:8]([N:10]([CH:12]([CH3:14])[CH3:13])[CH3:11])[CH2:9][C@H:4]2[NH:3][CH:1]=[O:2])[C:16]1=[O:31]

Participants

4

Reactant 1

HCID 86618152benzyl (S)-1-((1S,2R,4R)-2-formamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

Product 1

HCID 86618153N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)formamideYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl (S)-1-((1S,2R,4R)-2-formamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (50 mg, 0.116 mmol) in methanol (3 mL) was added 10% Pd/C (40 mg of 50% wet catalyst). The flask was evacuated and back-filled with hydrogen from a hydrogen balloon. The mixture was stirred at room temperature for 1 h and the catalyst was removed by filtration. The filtrate was concentrated in vacuo to provide N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)formamide (35 mg, 100%) which was taken on to the next step without further purification. LC/MS found [M+H]+=297.

Workup

  1. customThe flask was evacuated
  2. additionback-filled with hydrogen from a hydrogen balloon
  3. customthe catalyst was removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3596ae45159d4ee39a7a2052a0a22889
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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