Sodium Bicarbonate → HCID 67772265, compound

Participants

Reaction Steps

A 1 M solution of LAH in THF (66.8 mL, 66.8 mmol) under nitrogen was heated to 45° C. A solution of (S)-tert-butyl 1-cyclobutyl-2-(3-hydroxyazetidin-1-yl)-2-oxoethylcarbamate (Compound Y2.1) (3.80 g, 13.4 mmol) in THF (20 mL) was added dropwise over 30 min. The resultant mixture was stirred at 47° C. over night. The mixture was cooled on an ice-bath and NaHCO3 (8% aq., 16 mL) was carefully added dropwise. The stirring was continued for 2 h at rt. The precipitate was filtered off and washed with DCM. The filtrate was concentrated and the residue dissolved in DCM and filtered through a 0.45 μm syringe filter. The filtrate was concentrated to give the title compound (2.23 g, 91%, 92% pure) as an oil. 1H NMR (400 MHz, CD3OD) δ 1.69-2.13 (6H), 2.2-2.38 (7H), 2.79 (1H), 2.89 (1H), 3.56-3.66 (2H), 4.26-4.34 (1H). Expected Number of protons: 20. OH- and NH-protons are exchanged with CD3OD.

Provenance & Evidence