Water → N-(2-(1H-indol-3-yl)ethyl)-2-(tert-butyldimethylsilyloxy)ethanamine

HRID 564275Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[Si:13]([O:20][CH2:21][CH:22]=O)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl>[C:16]([Si:13]([CH3:15])([CH3:14])[O:20][CH2:21][CH2:22][NH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

Tryptamine (3.34 g, 20.85 mmol) and t-butyldimethylsilyloxylacetaldehyde (2.44 g, 13.99 mmol) is dissolved in dichloromethane (200 ml) for 10 minutes. The mixture is cooled to 0° C. and it is added sodium triacetoxyborohydride (5.38 g, 25.38 mmol). The mixture is warmed slowly to room temperature and stirred for 18 hours. Then water is added and the mixture is extracted with dichloromethane. The organic phase is dried over sodium sulfate, filtered and evaporated. The crude product is purified by a silica gel flash chromatograph using dichloromethane-methanol eluent.

Workup

temperatureThe mixture is warmed slowly to room temperature
extractionthe mixture is extracted with dichloromethane
dry with materialThe organic phase is dried over sodium sulfate
filtrationfiltered
customevaporated
customThe crude product is purified by a silica gel flash chromatograph

Sources & evidence

ORD record: ord-3d4af05cbc814aa19557ffbf285a5093
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067615B2

Reaction notes

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