Tetrahydrofuran → HCID 58697743, compound

Participants

Reaction Steps

A solution of the product of step 1 above (1 g, 2.9 mmol, 1 equiv) in THF anhydrous (15 mL) is cooled down to −78° C. and lithium bis(trimethylsilyl)amide 1.0 M in THF (3.2 mL, 3.2 mmol, 1.1 equiv) is added dropwise. The reaction mixture is stired at −78° C. for 1 h. (R)-(−)-Glycidal butyrate (466 mg, 0.46 mL, 3.2 mmol, 1.1 equiv) is added dropwise and the reaction mixture is allowed to gradually warm to room temperature and is left to stir over weekend. The mixture is quenched with saturated aqueous ammonium chloride (20 mL), diluted with water (30 mL) and extracted with EtOAc (3×50 mL). The washed organics with brine are dried over (MgSO4) and concentrated. The product is purified by flash chromatography on silica gel using 1–3% MeOH in DCM as eluant to give the title compound as a solid (380 mg, 1.24 mmol, 42.8%). HPLC Rt=4.36, MS=(M+H)+=307.

Provenance & Evidence