Acetic Acid → (2S,3R)-3-amino-1-[[3-(4-fluorophenyl)propyl](methyl)amino]butan-2-ol

HRID 1592364Notes

Reaction equation

HRID 1592364 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]([CH3:25])[C@@H:10]([OH:24])[CH2:11][N:12]([CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH3:13])C1C=CC=CC=1.CC(O)=O>CO.CCOCC.[OH-].[OH-].[Pd+2]>[NH2:8][C@H:9]([CH3:25])[C@@H:10]([OH:24])[CH2:11][N:12]([CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[CH3:13]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 58997715(2S,3R)-3-(dibenzylamino)-1-[[3-(4-fluorophenyl)propyl](methyl)amino]butan-2-ol

Product 1

HCID 58997707(2S,3R)-3-amino-1-[[3-(4-fluorophenyl)propyl](methyl)amino]butan-2-olYield 84.7%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Pd(OH)2 was carefully wetted down under N2 with 10 mL of MeOH then the product of Step f (1.15 g) dissolved in 40 mL of MeOH was added followed by 50 mL of HOAc. The mixture was hydrogenated overnight on a Parr shaker at 50 PSI. Worked up by filtering off the catalyst under N2 through a fiberglass filter paper and vacuum. The filtrate was stripped to obtain an oily residue which was dissolved in 25 mL of Et2O and washed 2 times with 1N NaOH, 1 time with brine, dried (Na2SO4) and stripped to give 0.57 g of a light yellow oil. MS (ESI) detects (M+H)+=255.

Workup

  1. additionwas added
  2. filtrationby filtering off the catalyst under N2 through a fiberglass
  3. filtrationfilter paper and vacuum
  4. customto obtain an oily residue which
  5. washwashed 2 times with 1N NaOH, 1 time with brine
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-49cfa3f6c04c42f7aa33d7ff594082ae
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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