HCID 20760149, compound → 4-{[(2R)-2,3-Dihydroxypropyloxy]phenyl}butylamine

HRID 25134Notes

Reaction equation

HRID 25134 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH2:23][C@H:24]([OH:27])[CH2:25][OH:26])(OCC1C=CC=CC=1)=O>CO.[Pd]>[OH:27][C@H:24]([CH2:25][OH:26])[CH2:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][CH2:14][CH2:13][CH2:12][NH2:11]

Participants

4

Reactant 1

HCID 20760149HCID 20760149, compound

Product 1

HCID 673657434-{[(2R)-2,3-Dihydroxypropyloxy]phenyl}butylamineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a vigorously stirred solution of 69 (2 g, 5.4 mmol) in methanol (60 mL) under nitrogen was added Pd/C (10% wet, 0.5 g). The mixture was stirred 2 h at room temperature under an atmosphere of hydrogen then the pressure was released and the mixture was filtered through a pad of silica gel. The solvent was removed and the residue was purified by column chromatography (silica gel, 2:1:0.2 chloroform/ethanol/concentrated ammonium hydroxide) to provide 70 (1.18 g, 92%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.32 (m, 2H), 1.54 (m, 2H) 2.55 (m, 2H), 3.45 (m, 2H), 3.82 (m, 3H), 3.94 (m, 2H), 6.83 (d, 2H), 7.08 (d, 2H).

Workup

  1. filtrationthe mixture was filtered through a pad of silica gel
  2. customThe solvent was removed
  3. customthe residue was purified by column chromatography (silica gel, 2:1:0.2 chloroform/ethanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-f10149303d994531bcc472a2ba339087
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

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