Ethanone, 1-phenyl-, dihydroxy deriv. → N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)aniline

HRID 51284Notes

Reaction equation

HRID 51284 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[CH:19](O)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].[BH3-]C#N.[Na+]>CO>[C:22]1([CH:20]([OH:21])[CH2:19][NH:15][C:14]2[CH:16]=[CH:17][C:11]([CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])=[CH:12][CH:13]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 99611Ethanone, 1-phenyl-, dihydroxy deriv.HCID 382207Tert-butyl 4-aminophenethylcarbamateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21959862N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)anilineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(N-Boc-2-aminoethyl)aniline 28 (1.25 g, 5.29 mmole) was dissolved in methanol (30 mL), followed by addition of phenyl glyoxal 24 (0.708 g, 5.28 mmole). The reaction mixture was stirred for 1 h at rt, prior to addition of NaCNBH3 (0.665 g, 10.6 mmole). The final mixture was stirred for 12 h at rt, concentrated, and purified by flash silica column chromatography (2 to 5% MeOH/CH2Cl2) to give N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)-aniline as a pale yellow oil (1.71 g, 91%): Rf=0.18 in 5% MeOH/CH2Cl2. 1H-NMR (CD3OD, 299.96 MHz): δ (ppm) 7.4-7.25 (m, 5H), 7.0-6.95 (d, 2H), 6.63-6.60 (d, 2H), 4.85-4.79 (dd, 1H), 3.3-3.21 (t, 2H), 3.2-3.15 (m, 2H), 2.64-2.5 (t, 2H), 1.42 (s, 9H).

Workup

  1. concentrationconcentrated
  2. custompurified by flash silica column chromatography (2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-58e5785065db4a12bbed314d206e0225
Source dataset
uspto-grants-2004_03
Patent number
US06713651B1

Reaction notes

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