Diisopropylethylamine → N'-[3-(t-Butyl-dimethyl-silanyloxy)-propyl]-N'-methyl-hydrazinecarboxylic acid t-butyl ester

HRID 240725Notes

Reaction equation

Cl.[CH3:2][C:3]([Si:6]([CH3:14])([CH3:13])[O:7][CH2:8][CH2:9][CH2:10][NH:11][CH3:12])([CH3:5])[CH3:4].C(N(CC)C(C)C)(C)C.[CH3:24][C:25]([O:28][C:29]([N:31]1C(C2C=CC(C#N)=CC=2)O1)=[O:30])([CH3:27])[CH3:26]>ClCCl>[C:25]([O:28][C:29]([NH:31][N:11]([CH2:10][CH2:9][CH2:8][O:7][Si:6]([C:3]([CH3:2])([CH3:4])[CH3:5])([CH3:13])[CH3:14])[CH3:12])=[O:30])([CH3:27])([CH3:26])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-N-methyl-1-propanamine hydrochloride (1:1) (720 mg, 3.0 mmol) was combined with dichloromethane (30 mL) to give a colorless solution. N,N-Diisopropylethylamine (313 mg, 423 μl, 2.42 mmol) was added at 0° C. Subsequently 3-(4-cyanophenyl)-2-oxaziridinecarboxylic acid 1,1-dimethylethyl ester (542 mg, 2.2 mmol) in dichloromethane (20 mL) was added during 15 min at 0° C. and the reaction mixture was stirred for 1 h at 0° C. Afterwards the reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 20 g, 0% to 70% ethyl acetate in n-heptane) to deliver an oil contaminated with 4-cyano-benzaldehyde. This material was purified by a second chromatography (aminophase 20 g, ethyl acetate/n-heptane 1/1) to give the title compound as colorless oil.

Workup

customto give a colorless solution
concentrationAfterwards the reaction mixture was concentrated in vacuo
customthe residue was purified by flash chromatography (silica gel, 20 g, 0% to 70% ethyl acetate in n-heptane)
customThis material was purified by a second chromatography (aminophase 20 g, ethyl acetate/n-heptane 1/1)

Sources & evidence

ORD record: ord-7e7ef1b71ded4ed297e21a149672eb96
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648099B2

Reaction notes

Loading…