Hydrochloric Acid → HCID 21021216, compound

HRID 1793791Notes

Reaction equation

HRID 1793791 reaction equation
[N:1]([CH2:4][C@H:5]([OH:18])[CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17])=[N+]=[N-].[ClH:19].[H][H]>[Pd].CCO>[ClH:19].[NH2:1][CH2:4][C@H:5]([OH:18])[CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21021235HCID 21021235, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21021216HCID 21021216, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To EtOH solution (80 ml) of N-(3-azido-2(R)-hydroxypropyl)phthalimide 1.96 g (7.69 mmol), 10% Pd—C (200 mg) and concentrated hydrochloric acid solution 1.4 ml were added sequentially. To the reaction mixture, hydrogen was introduced at 2 kgf/cm2 atm. and then stirring was continued at room temperature overnight. After removal of catalyst by filtration, catalyst was washed with EtOH/DMF (1:1) solution (60 ml) and then combined filtrate was evaporated to dryness. Addition of EtOH to the residue gave crystal of desired product as a hydrogen chloride salt. Crystal was collected by filtration and dried under reduced pressure at 40° C. to afford 1.28 g of the product. The NMR spectra were consistent with the desired title intermediate.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration, catalyst
  3. washwas washed with EtOH/DMF (1:1) solution (60 ml)
  4. customcombined filtrate was evaporated to dryness
  5. additionAddition of EtOH to the residue

Sources & evidence

ORD record
ord-77a214325a1d4fa49e25224dd344fb35
Source dataset
uspto-grants-2006_04
Patent number
US07022677B1

Reaction notes

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