Sodium borohydride → HCID 45083317, compound

Temperature

5 °C

A solution of 19 (80 mg, 0.42 mmol) in ethanol (5 mL) was added dropwise to a stirred solution of sodium periodate (150 mg, 0.7 mmol) in water (5 mL) at such a rate so as to maintain the reaction temperature at 5° C. On completion, sodium borohydride (135 mg, xs) was added portionwise to the resulting suspension at such a rate so as to maintain the reaction temperature at 0° C. and on complete addition the reaction was allowed to warm to r.t. Flash chromatography grade silica was added to the reaction and the resulting suspension was concentrated in vacuo to afford a white solid. The solid was purified by chromatography to afford 20 (51 mg, 76%) as a colourless oil. 1H NMR δ 4.43 (dd, J=5.7, 3.3 Hz, 1H), 3.91 (q, J=4.7 Hz, 1H), 3.75 (d, J=4.7 Hz, 1H), 3.31 (m, 1H), 3.28 (dd, J=11.8, 5.7 Hz, 1H), 2.75 (dd, J=11.8, 5.5 Hz, 1H), 2.17 (s, 3H). 13C NMR δ 173.9, 76.5, 68.2, 62.5, 55.8, 21.7. HRMS (MH+) calc. for C6H13N2O3: 161.0926. Found 161.0920.

1. temperatureto maintain the reaction temperature at 0° C.
2. additionon complete addition the reaction
3. temperatureto warm to r.t
4. additionFlash chromatography grade silica was added to the reaction
5. concentrationthe resulting suspension was concentrated in vacuo
6. customto afford a white solid
7. customThe solid was purified by chromatography

ORD record

ord-c054fe6d7fd44fbb9c44c1627fda866b

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173662B2