8-(6-Methoxy-[1,5]naphthyridin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-ol → 8-[2-(6-Methoxy-[1,5]naphthyridin-4-yl)ethyl]-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1354212Notes

Reaction equation

HRID 1354212 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C:13]#[C:14][C:15]1([OH:25])[CH2:24][CH2:23][C:18]2([O:22][CH2:21][CH2:20][O:19]2)[CH2:17][CH2:16]1.[H][H]>C(O)C.O=[Pt]=O>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][C:15]1([OH:25])[CH2:16][CH2:17][C:18]2([O:22][CH2:21][CH2:20][O:19]2)[CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 211046678-(6-Methoxy-[1,5]naphthyridin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-olHCID 178418361HCID 178418361, compound

Product 1

HCID 211046648-[2-(6-Methoxy-[1,5]naphthyridin-4-yl)ethyl]-1,4-dioxa-spiro[4.5]decan-8-ol

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 8-(6-methoxy-[1,5]naphthyridin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-ol (965 mg, 2.8 mmol) in ethanol (100 ml) was hydrogenated for 6 hours over PtO2 (200 mg) at 1 bar of hydrogen. The catalyst was filtered off and replaced by fresh catalyst and the hydrogenation was continued for a further 3 hours. The catalyst was filtered off and the solvent was concentrated. The crude product was purified by chromatography on silica gel (EtOAc).

Workup

  1. filtrationThe catalyst was filtered off
  2. filtrationThe catalyst was filtered off
  3. concentrationthe solvent was concentrated
  4. customThe crude product was purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-1c93d1b9bbd54b3ba19702f2923804ce
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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