Butyl bromide → (Z)-butoxyimino-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-oxidoazanium

Temperature

65 °C

To a suspension of sodium (2S)-2-(hydroxymethyl)-1-[(Z)-oxido-NNO-azoxy]pyrrolidine (447 mg, 2.44 mmol) and tetrabutylammonium iodide (90 mg, 0.24 mmol) in DMF (10 mL) was added 1-bromobutane (315 μL, 2.93 mmol). The resulting suspension was allowed to stir at 65° C. over night. After cooling to rt, the mixture was partitioned between Et2O (50 mL) and brine (50 mL). The organic layer was separated and washed with brine (2×50 mL), dried over MgSO4 and concentrated. The residue was purified by flash chromatography (Biotage 40+M) using 35-50% ethyl acetate in hexanes gradient, affording the title product: 1H NMR (500 MHz, CDCl3) δ 4.21 (t, J=6.7 Hz, 2H), 4.07-4.02 (m, 1H), 3.75 (dd, J=3.6, 11.3 Hz, 1H), 3.63-3.54 (m, 3H), 3.06 (br. s, 1H), 2.12-2.04 (m, 1H), 1.98-1.91 (m, 2H), 1.81-1.71 (m, 3H), 1.47-1.39 (m, 2H), 0.95 (t, J=7.4 Hz, 3H).

1. temperatureAfter cooling to rt
2. customthe mixture was partitioned between Et2O (50 mL) and brine (50 mL)
3. customThe organic layer was separated
4. washwashed with brine (2×50 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography (Biotage 40+M)

ORD record

ord-449ddfcfe68c431eb50ee8c5d03b1801

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08377911B2