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

HRID 453867Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.[CH:19]([C:21]1[N:22]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:23]([CH3:26])=[CH:24][CH:25]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:15]([O:14][C:12](=[O:13])[CH2:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][CH2:26][C:23]3[N:22]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:21]([CH3:19])=[CH:25][CH:24]=3)[CH:10]=2)[CH:6]=[CH:7]1)([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 25 °C

Procedure

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%

Workup

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

Sources & evidence

ORD record: ord-ecbc75095b5746b8a12ea3447593769c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492559B2

Reaction notes

Loading…