Sodium borohydride → HCID 21830758, compound

HRID 1600908Notes

Reaction equation

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH2:15][CH2:16][C:17](=[O:26])[CH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH:9]=[CH:8]2.[BH4-].[Na+]>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH2:15][CH2:16][CH:17]([OH:26])[CH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH:9]=[CH:8]2

Participants

Conditions

Temperature: 0 °C

Procedure

1-{6-(Methoxymethoxy)-2-naphthyl}-5-(3-pyridyl)-3-pentanone (1.9 g; from Example 31 above) was immediately dissolved in methanol (100 ml) and cooled to 0° C. Solid sodium borohydride (0.284 g) was added and the reaction mixture stirred at 25° C. for 2 hours. The mixture was concentrated under reduced pressure and water was added to the residue. The aqueous mixture was extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:methanol (95:5) to give an oil (0.94 g).

Workup

concentrationThe mixture was concentrated under reduced pressure and water
additionwas added to the residue
extractionThe aqueous mixture was extracted with ethyl acetate
dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography over silica eluting with dichloromethane:methanol (95:5)

Sources & evidence

ORD record: ord-0965176c03764604a506592970cbce67
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977105

Reaction notes

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