HCID 86640212, compound → HCID 67002108, compound

HRID 908269Notes

Reaction equation

HRID 908269 reaction equation
[CH2:1]([CH2:3][C:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]=[N+]=[N-])=[CH:10][CH:9]=1)([CH3:6])[CH3:5])[CH3:2]>CO.[Pd]>[CH2:1]([CH2:3][C:4]([O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH2:16])=[CH:12][CH:13]=1)([CH3:5])[CH3:6])[CH3:2]

Participants

4

Reactant 1

HCID 86640212HCID 86640212, compound

Product 1

HCID 67002108HCID 67002108, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C at 10% (16 mg) is added to a solution of ethyl 2-[4-(2-azidoethyl)phenoxy]-2-methylpropane (784 mg, 2.89 mM) in methanol (42 ml) and the suspension is maintained in agitation for the whole night at a pressure of 5 atmospheres of H2 at room temperature until the substrate disappears [TLC (silica gel; mobile phase: ethyl acetate/petroleum ether=2:8)]. The mixture is filtered to remove the catalyst and the solvent is removed at reduced pressure. 539 mg of ethyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropane is obtained as a colorless oil (74% of yield). FT-IR (neat): 3366, 2985, 2922, 2851, 1732, 1610, 1579, 1508, 1467, 1382, 1362, 1283, 1235, 1177, 1140, 1023, 971, 908, 836, 768 cm−1; 1H NMRs (400 MHz CD Cl3, δ): 7.06-7.04 (d, 2H, J=8.6 Hz, aromatic protons); 6.78-6.76 (d, 2H, J=8.6 Hz, aromatic protons); 5.70-5.55 (m, 2H, NH2); 4.25-4.19 (q, 2H, J=7.1 Hz, CH2CH3); 2.96-2.92 (t, 2H, J=7.0 Hz, CH2C6H4); 2.76-2.69 (m, 2H, CH2NH2); 1.56 (s, 6H, C(CH3)2); 1.26-1.22 (t, 3H, J=7.1 Hz, CH3CH2). 13C NMRs (100 MHz CDCl3, δ): 174.33, 153.84, 132.84, 129.42, 119.34, 79.04, 61.37, 43.07, 38.13, 25.32, 14.06. MS-ESI m/z (%): 252 [M+H]+(100). MS-MS (252): 235 (100), 121 (13).

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst
  3. customthe solvent is removed at reduced pressure

Sources & evidence

ORD record
ord-b595f666d70742c781c8ac02f02e86da
Source dataset
uspto-grants-2011_09
Patent number
US08017613B2

Reaction notes

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