Ethanol → HCID 59772980, compound

Participants

Reaction Steps

The catalyst (Aldrich Palladium, 5 wt % (dry basis) on activated carbon as 50 wt % suspension in water (Degussa type E101 NO/W), 3.0 g, 0.70 mmol) was charged to a flask, which was evacuated and purged with nitrogen three times. A solution of nitrile 1a (14.0 g, 45.4 mmol) in ethanol (450 ml) and concentrated aqueous ammonium hydroxide solution (31 wt %, 40 ml, 620 mmol) were added. The flask was evacuated and purged with nitrogen three times then evacuated and filled with hydrogen twice. The reaction was stirred at room temp under hydrogen at balloon pressure and monitored by TLC (5% methanol in DCM) until complete (1-2 days). When complete, the flask was evacuated and purged with nitrogen three times, the catalyst was filtered off through a glass fibre filter paper and washed with hot ethanol (3×100 ml). The reaction was worked up as follows: the filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (25 fold weight of silica based on crude product) using a gradient elution with 5-50% methanol in DCM which yielded 90% of [4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylsulfonyl)phenyl]methanamine 7b.

Provenance & Evidence