Methanol → 2-(hydroxymethyl)-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533151Notes

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]=[C:13]([CH:18]=C)[CH:12]=[CH:11][C:10]=3[C:9]2=[O:20])=[CH:5][CH:4]=1.C[OH:24].[BH4-].[Na+]>C(Cl)Cl>[OH:24][CH2:18][C:13]1[CH:12]=[CH:11][C:10]2[C:9](=[O:20])[N:8]([CH2:7][C:6]3[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:17][CH2:16][C:15]=2[N:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-(4-Methoxybenzyl)-2-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one (1 g, 4.49 mmol) from above was dissolved in a 1:1 mixture of DCM:MeOH, (50 mL) and cooled to −78° C. Ozone was bubbled through for 30 min. The reaction was warmed to 0° C. then NaBH4 (400 mg, 10.8 mmol) was added and the cold bath removed. After 10 min, the reaction mixture was quenched with Rochelle's Salt (20% solution, 50 mL) and diluted with EtOAc (100 mL). The organics were dried and concentrated to give 980 mg (96%). LC-MS (M+H)=299.1.

Workup

customOzone was bubbled through for 30 min
customthe cold bath removed
customthe reaction mixture was quenched with Rochelle's Salt (20% solution, 50 mL)
additiondiluted with EtOAc (100 mL)
customThe organics were dried
concentrationconcentrated
customto give 980 mg (96%)

Sources & evidence

ORD record: ord-5f18227d51784d758d777089a1de5fad
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853237B2

Reaction notes

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