Acetic Acid → 4-[(2,3-Diacetoxypropyloxy)phenyl]butylamine

HRID 81301Notes

Reaction equation

HRID 81301 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][CH:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:25][O:26][C:27](=[O:29])[CH3:28])(OCC1C=CC=CC=1)=O.C(O)(=O)C>CO.[Pd]>[C:31]([O:30][CH:24]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[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])(=[O:33])[CH3:32]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22566152HCID 22566152, compound

Product 1

HCID 225661724-[(2,3-Diacetoxypropyloxy)phenyl]butylamineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Cbz-protected amine 34 (0.6 g, 1.3 mmol) was dissolved in methanol (25 mL) containing 1% acetic acid then Pd/C (0.22 g, 5% wet.) was added. The reaction mixture was stirred for 3 h under hydrogen (1 atm), then the solution was filtered through a pad of silica gel and the solvent was evaporated to give amine 35 (0.37 g, 86%) as a clear oil.

Workup

  1. filtrationthe solution was filtered through a pad of silica gel
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7f1e0bf38a854fb1868fbb0bae19c7ab
Source dataset
uspto-grants-2014_09
Patent number
US08846688B2

Reaction notes

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