tert-Butyl 4-((1S)-1-{[(benzyloxy)carbonyl]amino}ethyl)benzoate → tert-butyl 4-[(1S)-1-aminoethyl]benzoate

HRID 1293180Notes

Reaction equation

HRID 1293180 reaction equation
C(OC([NH:11][C@H:12]([C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1)[CH3:13])=O)C1C=CC=CC=1>C(O)C.C(O)(=O)C.[C].[Pd]>[NH2:11][C@H:12]([C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[CH:16][CH:15]=1)[CH3:13]

Participants

5

Reactant 1

HCID 69048022tert-Butyl 4-((1S)-1-{[(benzyloxy)carbonyl]amino}ethyl)benzoate

Product 1

HCID 51358470tert-butyl 4-[(1S)-1-aminoethyl]benzoateYield 93.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a stirred solution of tert-butyl 4-((1S)-1-{[(benzyloxy)carbonyl]amino}ethyl)benzoate (step 2, 3.48 g, 9.8 mmol) in a mixture of ethanol (25 mL) and acetic acid (25 mL) was added 10% palladium-carbon (400 mg). The mixture was stirred at room temperature for 2 h under hydrogen atmosphere. The palladium catalyst was removed by filtration and washed with ethanol (100 mL). The filtrate was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (200 mL) and saturated sodium bicarbonate aqueous solution (200 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (200 mL). The combined organic extracts were washed with brine (200 mL) and dried (sodium sulfate), and concentrated to give 2.02 g (93%) of the title compounds as white solids: 1H-NMR (CDCl3) δ 7.95 (2H, d, J=8.3 Hz), 7.39 (2H, d, J=8.3 Hz), 4.22–4.12 (1H, dq, J=7.3, 6.6 Hz), 1.80 (2H, br.s), 1.58 (9H, s), 1.38 (3H, d, J=6.6 Hz).

Workup

  1. customThe palladium catalyst was removed by filtration
  2. washwashed with ethanol (100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate (200 mL) and saturated sodium bicarbonate aqueous solution (200 mL)
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with ethyl acetate (200 mL)
  7. washThe combined organic extracts were washed with brine (200 mL)
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-302744cbcc6b4677a5fd805ca183f497
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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