Ammonium Chloride → HCID 11224101, compound

Participants

Reaction Conditions

Reaction Steps

To a mechanically stirred mixture of 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-nitroindol-1-yl)-2-butyl]imidazole-4-carboxamide (450 mg, 0.98 mmol) and ammonium chloride (45 mg) in ethanol (10 ml) and water (5 ml) was added portionwise iron powder (450 mg) at 90° C. The resulting mixture was stirred for 40 minutes at 90° C. After cooling, the insoluble material was filtered through Celite and washed with ethanol and ethyl acetate. The filtrate and the washing were combined and concentrated in vacuo. The resulting residue was extracted with ethyl acetate and washed with brine. The organic layer was dried (sodium sulfate) and concentrated in vacuo to give 1-[(R)-4-(6-aminoindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide (397 mg, 94.7%). This material was used for the next reaction without further purification.

Provenance & Evidence