Hydrochloric Acid → (2S,3R)-4-Amino-2-dibenzylamino-1-phenyloct-7-en-3-ol

HRID 1436730Notes

Reaction equation

HRID 1436730 reaction equation
[CH2:1]([N:8]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@H:9]([C@H:17]([OH:26])[CH:18]([N+:23]([O-])=O)[CH2:19][CH2:20][CH:21]=[CH2:22])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C.[Zn]>[NH2:23][CH:18]([CH2:19][CH2:20][CH:21]=[CH2:22])[C@@H:17]([OH:26])[C@@H:9]([N:8]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69018478(2S,3S)-2-dibenzylamino-4-nitro-1-phenyloct-7-en-3-ol

Product 1

HCID 69017314(2S,3R)-4-Amino-2-dibenzylamino-1-phenyloct-7-en-3-ol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Add powdered Zn (1.56 g, 24 mmol) portionwise at 0-5° C. to a stirred suspension of the (2S,3S)-2-dibenzylamino-4-nitro-1-phenyloct-7-en-3-ol mixture (2.7 g, 6 mmol) in a mixture of ethanol (20 mL) and concentrated HCl (20 mL). Stir for 1 h. Filter the reaction mixture and concentrate the filtrate under reduced pressure. Dilute residue with water and add concentrated ammonium hydroxide. Extract with dichloromethane. Wash the organic layer with water, dry (magnesium sulfate), and concentrate under reduced pressure to give the mixture of amines (1.5 g, 60%).

Workup

  1. filtrationFilter the reaction mixture
  2. concentrationconcentrate the filtrate under reduced pressure
  3. additionDilute residue with water and add concentrated ammonium hydroxide
  4. extractionExtract with dichloromethane
  5. washWash the organic layer with water
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate under reduced pressure
  8. customto give

Sources & evidence

ORD record
ord-47a5d66ce0e74c1ebbefeeab1a3156e1
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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