Hydrochloric Acid → 2-(3-amino-2-hydroxypropyl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride

HRID 1793789노트

반응식

HRID 1793789 반응식
[N:1]([CH2:4][CH: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].C(O)C>[ClH:19].[NH2:1][CH2:4][CH: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]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 10857754N-(3-Azido-2-hydroxypropyl)phthalimideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 222191282-(3-amino-2-hydroxypropyl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To ethanol solution (240 ml) of N-(3-azido-2-hydroxypropyl)phthalimide 10 g (40.3 mol), 10% Pd—C (1 g) and concentrated hydrochloric acid solution 7.84 ml (80.6 mmol) were added sequentially. To the reaction mixture, hydrogen was introduced at 2 kgf/cm2 atm. and hydrogenated at room temperature for 6 hours. After removal of catalyst by filtration, catalyst was washed with EtOH/DMF (1:1) solution (300 ml) and then combined filtrate was evaporated to dryness. Addition of EtOH to the residue gave crystal of desired product as hydrogen chloride salt. Crystal was collected by filtration and dried under reduced pressure at 40° C. to afford 5.3 g of the product. The NMR spectra were consistent with the desired title intermediate.

후처리

  1. customAfter removal of catalyst
  2. filtrationby filtration, catalyst
  3. washwas washed with EtOH/DMF (1:1) solution (300 ml)
  4. customcombined filtrate was evaporated to dryness
  5. additionAddition of EtOH to the residue

출처 및 근거

ORD 기록
ord-5014fafc69d046df8906319f48d0ad7c
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022677B1

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