Methanol → 3-(hydroxymethyl)-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one
Reaction equation
[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]=1Participants
4
Procedure
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.
Workup
- customA stream of O3 was bubbled through for 20 min
- customconsumption of starting material
- additionNaBH4 (500 mg) was added to the solution
- customthe cold bath removed
- waitAfter 20 min
- additionRochelle's salt (20%, 5 mL) was added to the reaction mixture
- concentrationThe mixture was concentrated
- dry with materialdried over MgSO4
- concentrationThe filtrate was concentrated
- customused directly in the next step without further purification (800 mg, 98%)
Sources & evidence
- ORD record
- ord-4802632f0b1f420b96633bbdda118524
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853237B2
Reaction notes
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