Acryloyl chloride → tert-butyl 4-allyl-4-(N-((1-tosyl-1H-indol-4-yl)methyl)acrylamido)piperidine-1-carboxylate

HRID 41561Notes

Reaction equation

[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH2:6]([C:9]1([NH:22][CH2:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[CH:27][N:28]3[S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH:7]=[CH2:8].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:6]([C:9]1([N:22]([CH2:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[CH:27][N:28]3[S:33]([C:36]2[CH:37]=[CH:38][C:39]([CH3:40])=[CH:41][CH:42]=2)(=[O:34])=[O:35])[C:1](=[O:4])[CH:2]=[CH2:3])[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)[CH:7]=[CH2:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Acryloyl chloride (0.360 g, 0.401 mmol) was added at 0° C. to a stirred solution of tert-butyl 4-allyl-4-((1-tosyl-1H-indol-4-yl)methylamino)piperidine-1-carboxylate (0.2 g, 0.382 mmol), diisopropylethylamine (0.32 mL, 1.91 mmol) in dichloromethane (5.0 mL). The reaction mixture was stirred at 0° C. for 30 min and was then allowed to warm to it and stirred for 4 h. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography (eluent: 5% ethyl acetate in hexane) to yield the title compound as a white solid (0.16 g, 72%). [LCMS RtE=0.774 min, [M+H-Boc]+=477.9]

Workup

temperatureto warm to it
stirringstirred for 4 h
concentrationThe reaction mixture was concentrated under reduced pressure
customthe crude product was purified by column chromatography (eluent: 5% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-6f870142bf734f6287936f27e13d63d5
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530648B2

Reaction notes

Loading…