Sodium Cyanide → HCID 178519557, compound

Participants

Reaction Steps

The following preparation followed the procedure by Horne et al., Heterocycles 39:139 (1994). A solution of the aldehyde (Intermediate R5; 0.34 g, 1.3 mmol) in EtOH (5 mL) was treated with tosylmethyl isocyanide (TosMIC; Aldrich; 0.25 g; 1.3 mmol) and NaCN (˜15 mg, cat) and allowed to stir at room temperature for 20 minutes. The solvent was removed in vacuo; the residue was dissolved in ˜7M NH3 in MeOH and transferred to a resealable tube before heating at 100° C. for 15 hours. The mixture was concentrated and purified by chromatography on SiO2 with 5% MeOH (sat. w/NH3):CH2Cl2. A solution of the product in THF with TBAF (1.5 eq.) was stirred at room temperature after aqueous workup. The crude product was chromatographed (5-7% NH3/MeOH in CH2C12) and designated Compound 2.

Provenance & Evidence