Methanol → 3-(hydroxymethyl)-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533163ノート

反応式

HRID 533163 の反応式
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[N:14]=[CH:13][C:12]([CH:18]=C)=[CH:11][C:10]=3[C:9]2=[O:20])=[CH:5][CH:4]=1.C(Cl)Cl.C[OH:27]>>[OH:27][CH2:18][C:12]1[CH:13]=[N:14][C:15]2[CH2:16][CH2:17][N:8]([CH2:7][C:6]3[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:9](=[O:20])[C:10]=2[CH:11]=1

参加物

4

反応物 3

HCID 887MethanolHCID 6344DichloromethaneHCID 680082206-(4-methoxybenzyl)-3-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one

生成物 1

HCID 680080933-(hydroxymethyl)-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

実験手順

6-(4-Methoxybenzyl)-3-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one (800 mg, 4.23 mmol) was dissolved in 1:1 MeOH:DCM (50 mL) and cooled in a dry ice/acetone bath. A stream of O3 was bubbled through for 20 min. At this time LC-MS indicated complete consumption of starting material. Oxygen was passed through the solution for 20 min, and then NaBH4 (500 mg) was added to the solution and the cold bath removed. After 20 min, Rochelle's salt (20%, 5 mL) was added to the reaction mixture. The mixture was concentrated and re-suspended into EtOAc (50 mL) and dried over MgSO4. The filtrate was concentrated and used directly in the next step without further purification (800 mg, 98%). LC-MS (M+H) =299.1.

後処理

  1. customA stream of O3 was bubbled through for 20 min
  2. customconsumption of starting material
  3. additionNaBH4 (500 mg) was added to the solution
  4. customthe cold bath removed
  5. waitAfter 20 min
  6. additionRochelle's salt (20%, 5 mL) was added to the reaction mixture
  7. concentrationThe mixture was concentrated
  8. dry with materialdried over MgSO4
  9. concentrationThe filtrate was concentrated
  10. customused directly in the next step without further purification (800 mg, 98%)

出典と根拠

ORDレコード
ord-4802632f0b1f420b96633bbdda118524
出典データセット
uspto-grants-2014_10
特許番号
US08853237B2

反応ノート

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