Ammonium formate → (2S)-1-(4-tert-butylphenyl)propan-2-amine

HRID 10193Notes

Reaction equation

HRID 10193 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2OC(=O)[NH:13][C@H:12]2[CH3:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C@@H:12]([NH2:13])[CH3:17])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69222385(4S,5S)-5-(4-tert-butylphenyl)-4-methyloxazolidin-2-one

Product 1

HCID 42054228(2S)-1-(4-tert-butylphenyl)propan-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1 g (4.3 mmole)(4S,5S)-5-(4-tert-butylphenyl)-4-methyl-oxazolidin-2-one p(see preparation 4, step 2), 2 g (31.74 mmole) ammonium formate and 0.1 g 10% palladium on carbon in 25 mL methanol was heated under reflux for 2 hrs. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was partitioned between 10 mL 10% sodium carbonate and 25 mL ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The title compound was isolated as the hydrochloride salt from diethyl ether, 0.93 g (95%), m.p.259.5–261.3° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was partitioned between 10 mL 10% sodium carbonate and 25 mL ethyl acetate
  6. dry with materialThe organic phase was dried (magnesium sulfate)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc2ed7cb3777480f9d07a2be12a3c96f
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

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