Diisopropylethylamine → tert-butyl (S)-2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinylamino)-3-cyclohexylpropylcarbamate

HRID 2355354Notes

Reaction equation

HRID 2355354 reaction equation
Cl.COCCCOC(C1C=CC=CC=1)C1CCCNC1.CSC(SC)=C[N+]([O-])=O.C(N(C(C)C)CC)(C)C.[CH3:39][O:40][CH2:41][CH2:42][CH2:43][O:44][CH:45]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH:46]1[CH2:51][CH2:50][CH2:49][N:48](/[C:52](/SC)=[CH:53]/[N+:54]([O-:56])=[O:55])[CH2:47]1.[NH2:65][C@@H:66]([CH2:76][CH:77]1[CH2:82][CH2:81][CH2:80][CH2:79][CH2:78]1)[CH2:67][NH:68][C:69](=[O:75])[O:70][C:71]([CH3:74])([CH3:73])[CH3:72]>C(#N)C>[CH3:39][O:40][CH2:41][CH2:42][CH2:43][O:44][CH:45]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH:46]1[CH2:51][CH2:50][CH2:49][N:48]([C:52]([NH:65][C@@H:66]([CH2:76][CH:77]2[CH2:78][CH2:79][CH2:80][CH2:81][CH2:82]2)[CH2:67][NH:68][C:69](=[O:75])[O:70][C:71]([CH3:74])([CH3:72])[CH3:73])=[CH:53][N+:54]([O-:56])=[O:55])[CH2:47]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 59382910tert-butyl (S)-2-amino-3-cyclohexylpropylcarbamateHCID 593830233-((3-methoxypropoxy)(phenyl)methyl)-1-((Z)-1-(methylthio)-2-nitrovinyl)piperidineHCID 668619713-((3-Methoxypropoxy)(phenyl)methyl)piperidine hydrochloride

Product 1

HCID 86626193tert-butyl (S)-2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinylamino)-3-cyclohexylpropylcarbamateYield 6.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-((3-Methoxypropoxy)(phenyl)methyl)piperidine hydrochloride (177 mg, 0.59 mmol), 1,1-bis(methylthio)-2-nitroethene (117 mg, 0.71 mmol, 1.2 equiv), and diisopropylethylamine (500 μL, 2.8 mmol, 5 equiv) were dissolved in acetonitrile (5 mL) and put on a shaker for 2 h. LC-MS indicated the presence of 3-((3-methoxypropoxy)(phenyl)methyl)-1-((Z)-1-(methylthio)-2-nitrovinyl)piperidine. Tert-butyl (S)-2-amino-3-cyclohexylpropylcarbamate (˜300 mg, 1.17 mmol, 2 equiv) was added to the mixture and shaking was continued overnight. The mixture was concentrated and purified by prep HPLC to afford tert-butyl (S)-2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinylamino)-3-cyclohexylpropylcarbamate (22 mg, 6.6%). LC-MS (3 min) tR=1.92 min. m/z 589 (M+1).

Workup

  1. waitwas continued overnight
  2. concentrationThe mixture was concentrated
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-fab86e31766b49a3b3e4208ec7f9d6d2
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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