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

HRID 1931063Notes

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-8dba06087c25492bba29f38de920ab04
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188138B2

Reaction notes

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