Pentane → 2-(2,5-Dimethylpyrrol-1-yl)-5-oxiranylpyridine

HRID 2102354Notes

Reaction equation

Cl[CH2:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])=[CH:9][CH:10]=1)=[O:4].[BH4-].[Na+].[OH-].[Na+].CCCCC>C1COCC1>[CH3:17][C:12]1[N:11]([C:8]2[CH:9]=[CH:10][C:5]([CH:3]3[CH2:2][O:4]3)=[CH:6][N:7]=2)[C:15]([CH3:16])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To the ketone from example 39 (1.34 g, 5.4 mmol) dissolved in dry THF (20 ml), cooled to 0° C., was added sodium borohydride (308 mg, 8.1 mmol) portionwise. The reaction mixture was stirred for 2 hours then 3M NaOH (aq) (10 ml) was added and stirring continued for a further 16 hours. The reaction mixture was extracted with ethyl acetate (2×29 ml) and the combined organic extracts washed with brine (5 ml), dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica eluting with ethyl acetate; pentane (1:5) to give the title compound as a colourless oil (900 mg, 4.2 mmol, 78%). 1H NMR (CDCl3, 400 MHz) δ: 2.13 (s, 6H), 2.91 (dd, 1H), 3.25 (t, 1H), 3.98 (t, 1H), 5.90 (s, 2H), 7.20 (d, 1H), 7.62 (dd, 1H), 8.58 (s, 1H). LRMS: m/z 215 (M-H+).

Workup

stirringstirring
waitcontinued for a further 16 hours
extractionThe reaction mixture was extracted with ethyl acetate (2×29 ml)
washthe combined organic extracts washed with brine (5 ml)
dry with materialdried over anhydrous magnesium sulphate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record: ord-18ef5287ffe34f20bc40fdd6157374ca
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576081B2

Reaction notes

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