Ammonia → HCID 86743463, compound

Participants

Reaction Steps

Under argon, 320 mg (8 mmol) of lithium aluminum hydride is suspended in 20 ml of absolute, freshly distilled tetrahydrofuran. At room temperature, a solution of 1.53 g (4 mmol) of 1,1-diethyl-3(1,6-dimethyl-2-formyl-8α-ergolinyl)urea in 40 ml of freshly distilled, absolute tetrahydrofuran is added dropwise. Subsequently the mixture is stirred for 1 1/4 hours at room temperature. The batch is then cooled in an ice bath and combined with 20 ml of 1N hydrochloric acid. To this is added 20 ml of 2N tartaric acid and the batch is layered over with ethyl acetate. For neutralizing, 80 ml of 2N ammonia solution is added dropwise. The ethyl acetate phase is separated and the aqueous phase additionally extracted with ethyl acetate. The combined ethyl acetate phases are dried over sodium sulfate. The concentrated crude product is chromatographed under pressure on silica gel with methylene chloride/methanol 95:5. The crude product (1.0 g) is crystallized from ethyl acetate, thus obtaining 0.72 g of 1,1-diethyl-3-(1,6-dimethyl-2-hydroxymethyl-8α-ergolinyl)urea (47% yield).

Provenance & Evidence