Sodium borohydride → (3R,4S)-2-Acetyl-4-hydroxy-3-hydroxymethyl-pyrazolidine

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence