Sodium triacetoxyborohydride → tert-butyl 2-((1-(2-tert-butoxy-2-oxoethyl)-1H-indol-6-ylamino)methyl)-5-methyl-1H-pyrrole-1-carboxylate

Temperature

25 °C

A solution of tert-butyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate A—for synthesis see above) (1.7368 mmol, 1.1 equiv.) in DCM (3 ml) was added at 0° C. to tert-butyl 2-formyl-5-methyl-1H-pyrrole-1-carboxylate (1.5789 mmol, 1.0 equiv.), dissolved in DCM (12 ml), and the mixture was stirred for 30 min at 25° C. At 0° C., Na(OAc)3BH (4.7368 mmol, 3.0 equiv.) was added in portions, and then the mixture was stirred for 12 h at 25° C. The reaction mixture was diluted with DCM (100 ml), washed with water and sat. NaCl solution (in each case 2×50 ml), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (5% ethyl acetate in hexane). Yield: 58%

1. stirringthe mixture was stirred for 12 h at 25° C
2. washwashed with water and sat. NaCl solution (in each case 2×50 ml),
3. dry with materialdried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customThe crude product was purified by column chromatography (5% ethyl acetate in hexane)

ORD record

ord-ecbc75095b5746b8a12ea3447593769c

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492559B2