HCID 57539226, compound → HCID 23649017, compound

HRID 2096912Notes

Reaction equation

HRID 2096912 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]([CH2:20][O:21][CH:22]([F:24])[F:23])[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]([CH2:20][O:21][CH:22]([F:23])[F:24])[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

4

Reactant 1

HCID 57539226HCID 57539226, compound

Product 1

HCID 23649017HCID 23649017, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

2-(Dibenzylamino)-3-(difluoromethoxy)-N-benzylpropanamide (362 mg, 0.863 mmol) was stirred with 10% Pd(OH)2 (200 mg) in ethanol under H2 overnight. The reaction mixture was filtered and concentrated to give 2-amino-N-benzyl-3-(difluoromethoxy)propanamide (195 mg, 93.6%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.83 (t, 1H), 7.25-7.40 (m, 5H), 6.27 (wt, 1H), 4.49 (d, 2H), 4.19 (d, 2H) and 3.68 (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-41b92984edb74b6495f68d9d692bdf50
Source dataset
uspto-grants-2013_05
Patent number
US08450336B2

Reaction notes

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