Ammonium Chloride → benzyl (3-(2-amino-1-(6-bromo-1H-indol-3-yl)propyl)-2-methylphenyl)carbamate

A solution of benzyl (3-(1-(6-bromo-1H-indol-3-yl)-2-nitropropyl)-2-methylphenyl)carbamate (4.47 g, 8.56 mmol), ammonium chloride (6.87 g, 128 mmol), and zinc dust (8.40 g, 128 mmol) in methanol (100 mL) and tetrahydrofuran (100 mL) was stirred overnight under nitrogen. The reaction was diluted with ethyl acetate and filtered through a pad of CELITE®. The filtrate was concentrated under reduced pressure, and the residue was diluted with ethyl acetate (150 mL), washed with saturated aqueous sodium bicarbonate (70 mL), and washed with brine (70 mL). The organic layer was collected, and the aqueous layers were sequentially extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give benzyl (3-(2-amino-1-(6-bromo-1H-indol-3-yl)propyl)-2-methylphenyl)carbamate (4.00 g, 8.12 mmol, 95% yield) as a light brown semi-solid and as a ˜1:1 diastereomers. LC/MS M+1=492.1 and 494.1.

1. filtrationfiltered through a pad of CELITE®
2. concentrationThe filtrate was concentrated under reduced pressure
3. additionthe residue was diluted with ethyl acetate (150 mL)
4. washwashed with saturated aqueous sodium bicarbonate (70 mL)
5. washwashed with brine (70 mL)
6. customThe organic layer was collected
7. extractionthe aqueous layers were sequentially extracted with ethyl acetate (2×100 mL)
8. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-a86ebeae2c6e42b98bab8470777bf783

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685969B2