Methanol → HCID 86639016, compound

Participants

Reaction Steps

To 1-(2,3,5-tri-O-benzyl-D-ribofuranosyl)-4-iodopyrrole-2-carbaldehyde in dichloromethane (15 ml), BBr3 (1 M, 8.5 ml) was added at −78° C. The reaction mixture was stirred for 2 hours, followed by addition of 50% methanol in CH2Cl2 (30 ml). After this solution was stirred at −78° C. for 10 minutes, 28% NH4OH (4 ml) was added and the reaction mixture was stirred until it reached room temperature. The solution was added to CH2Cl2 and H2O. The aqueous layer was partitioned and washed three times with CH2Cl2, and the residue was concentrated under reduced pressure. The product was purified by reversed-phase C18 HPLC to give 1-(β-D-ribofuranosyl)-4-iodopyrrole-2-carbaldehyde (330 mg).

Provenance & Evidence