Ammonium formate → (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine

HRID 429815Notes

Reaction equation

HRID 429815 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([C@H](C3C=CC=CC=3)C)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.C([O-])=O.[NH4+]>[Pd].C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([NH:13][CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57246230(S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-phenylethyl)amine

Product 1

HCID 11106515(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamineYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-phenylethyl)amine (23 grams, 0.074 mole) and ammonium formate (30 grams, 0.48 mole) and 10% palladium on carbon (3.7 grams) in ethanol (300 ml) was heated under reflux for 2 hours. The mixture was filtered and the solvent was evaporated to give a residue which was partitioned between 5% sodium hydroxide and ether. Evaporation of the organic phase gave (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine as an oil (14 grams, 92%), M+ 205.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe mixture was filtered
  4. customthe solvent was evaporated
  5. customto give a residue which
  6. customwas partitioned between 5% sodium hydroxide and ether
  7. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-ea39330baf954d839574e6dd8c88c934
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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