Imidazole → 3-{[tert-butyl(diphenyl)silyl]oxy}-N-(2-nitrobenzyl) propan-1-amine

HRID 2237463Notes

Reaction equation

[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][CH2:8][CH2:9][CH2:10][OH:11])([O-:3])=[O:2].N1C=CN=C1.[C:21]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])([CH3:23])[CH3:22]>ClCCl>[Si:25]([O:11][CH2:10][CH2:9][CH2:8][NH:7][CH2:6][C:5]1[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=1[N+:1]([O-:3])=[O:2])([C:21]([CH3:24])([CH3:23])[CH3:22])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 3-[(2-nitrobenzyl)amino]propan-1-ol (1.1 g, 5.0 mmol) in dichloromethane (50 mL) was treated with imidazole (0.68 g, 10 mmol) and tert-butylchlorodiphenylsilane (1.4 mL, 5.5 mmol) and stirred at 23° C. for 2 hours. The reaction mixture was quenched by the addition of H2O (50 mL) and 2 M aqueous NaOH (10 mL), and extracted with dichloromethane (2×50 mL), dried (Na2SO4), and evaporated. Flash chromatography (SiO2, 5-50% ethyl acetate/hexanes) provided 3-{[tert-butyl(diphenyl)silyl]oxy}-N-(2-nitrobenzyl) propan-1-amine (1.8 g, 80%) as a yellow oil:

Workup

customThe reaction mixture was quenched by the addition of H2O (50 mL) and 2 M aqueous NaOH (10 mL)
extractionextracted with dichloromethane (2×50 mL)
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-ebc18e0f69174926bcec5689c4cf7899
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718652B2

Reaction notes

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