tert-butyl (S)-2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinylamino)-3-cyclohexylpropylcarbamate → (2S)-N2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinyl)-3-cyclohexylpropane-1,2-diamine

HRID 2355355Notes

Reaction equation

HRID 2355355 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([NH:19][C@@H:20]([CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:21][NH:22]C(=O)OC(C)(C)C)=[CH:15][N+:16]([O-:18])=[O:17])[CH2:9]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([NH:19][C@@H:20]([CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:21][NH2:22])=[CH:15][N+:16]([O-:18])=[O:17])[CH2:9]1

Participants

3

Reactant 1

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

Product 1

HCID 68708709(2S)-N2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinyl)-3-cyclohexylpropane-1,2-diamineYield 126.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Tert-butyl (S)-2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinylamino)-3-cyclohexylpropylcarbamate (12 mg, 0.02 mmol) was dissolved in 1:1 TFA/CH2Cl2 (3 mL) and stirred for 30 min at rt. LC-MS showed the reaction was complete. After concentration, the mixture was purified by prep HPLC to afford (2S)—N2-(1-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)-2-nitrovinyl)-3-cyclohexylpropane-1,2-diamine (12.4 mg, 68%). LC-MS (3 min) tR=1.38 min. m/z 489 (M+1).

Workup

  1. concentrationAfter concentration
  2. customthe mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-40011d9004a94411b106cc198102e8ba
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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