Acetic Acid → HCID 23153085, compound

HRID 492921Notes

Reaction equation

HRID 492921 reaction equation
[C:1]([N:8]1[CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:13]([O:17][C:18]([NH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O)(=O)C>CO.[C].[Pd]>[C:13]([O:17][C:18]([NH:20][CH:21]1[CH2:22][CH2:23][N:24]([CH:10]2[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)[CH2:25][CH2:26]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7238334-(N-Boc-amino)piperidineHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 23153085HCID 23153085, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To 1-Boc-azetidin-3-on (1.00 g) and 4-(tert-butoxycarbonylamino)piperidine (1.17 g) dissolved in methanol (50 ml) were added acetic acid (0.368 ml) and 10% palladium carbon (1.0 g), followed by stirring under hydrogen atmosphere at room temperature for 12 hours. The reaction mixture was stirred under hydrogen atmosphere (0.4 MPa) at room temperature for 4 hours. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under reduced pressure. Ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate were added thereto, followed by partition. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated. The resultant crystals were suspended in diethyl ether-hexane, collected by filtration, and washed with hexane. There crystals were dried under aeration to provide the title compound (1.21 g) as colorless crystals.

Workup

  1. stirringThe reaction mixture was stirred under hydrogen atmosphere (0.4 MPa) at room temperature for 4 hours
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionEthyl acetate and a saturated aqueous solution of sodium hydrogencarbonate were added
  6. customby partition
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationThe organic layer was concentrated
  11. filtrationcollected by filtration
  12. washwashed with hexane
  13. customThere crystals were dried under aeration

Sources & evidence

ORD record
ord-fcc44757a282443e88daf1aa5057543e
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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