Dimethylformamide → 2-t-Butoxycarbonyl-9-allyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 2301089Notes

Reaction equation

CN(C=O)C.[C:6]([O:10][C:11]([N:13]1[CH2:25][CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[H-].[Na+].[CH2:28](Br)[CH:29]=[CH2:30]>C(OCC)(=O)C>[C:6]([O:10][C:11]([N:13]1[CH2:25][CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:30][CH:29]=[CH2:28])[C:15]=2[CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: -60 °C

Procedure

Anhydrous DMF solution (10 ml) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (4.40 g, 16.2 mmol) was mixed with 60% sodium hydride (700 mg, 10 mmol) and stirred at roam temperature for 1 hour. The reaction solution was cooled to −60° C., mixed with allyl bromide (2.18 g, 18 mmol) and then returned to room temperature by further stirring for 1 hour. The reaction solution was mixed with ethyl acetate (150 ml), washed with water and dried with anhydrous sodium sulfate, and then the solvent was removed by evaporation under a reduced pressure. The thus obtained residue was purified by a silica gel chromatography to obtain 4.32 g of the title compound as an oil (13.8 mmol, 87% in yield).

Workup

customreturned to room temperature
stirringby further stirring for 1 hour
washwashed with water
dry with materialdried with anhydrous sodium sulfate
customthe solvent was removed by evaporation under a reduced pressure
customThe thus obtained residue was purified by a silica gel chromatography

Sources & evidence

ORD record: ord-72c13789bf5047c3a75a7f70617097df
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498251B1

Reaction notes

Loading…