HCID 10734703, compound → HCID 10851554, compound

HRID 235204Notes

Reaction equation

HRID 235204 reaction equation
[N:1]([CH:4]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:13]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+]=[N-]>CO.[Pt]=O>[NH2:1][CH:4]([C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:17]=1)[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 10734703HCID 10734703, compound

Product 1

HCID 10851554HCID 10851554, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

To a solution of 3.10 g of methyl 4-[4-(1-azido-2-phenylethyl)phenyl]butyrate in 30 ml of methanol, 31 mg of platinum oxide was added, and hydrogenation was carried out at an ordinary temperature and under ordinary pressure for 4.5 hours. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure. The residue was added with dilute hydrochloric acid and washed with ether. The aqueous layer was made alkaline with potassium carbonate and then extracted with ether. The ether layer was washed with water and dried, and then the solvent was removed under reduced pressure to yield 2.16 g of brown oil.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was added with dilute hydrochloric acid
  4. washwashed with ether
  5. extractionextracted with ether
  6. washThe ether layer was washed with water
  7. customdried
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-37e6a5b58abe40c5a761fee624adaaed
Source dataset
uspto-grants-1997_01
Patent number
US05597848

Reaction notes

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