Methylhydrazine → O-(3-((tert-Butyldimethylsilyl)oxy)propyl)hydroxylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-isoindole-1,3-dione (26.3 g, 78.3 mmol) in dichloromethane (120 mL) was cooled to 0° C. and treated with methylhydrazine (16.1 g, 78.3 mmol). The reaction mixture was stirred for 30 min at 0° C. and filtered. The filtrate was concentrated under reduced pressure, redissolved in ether, and refrigerated (4° C.) overnight. The resultant crytalline material was removed by filtration and the filtrate was concentrated under reduced pressure to afford O-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-hydroxylamine (15.95 g, 99% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 4.69 (br s,2H), 3.74 (t, J=6.3 Hz, 2H), 3.67 (t, J=6.3 Hz, 2H), 1.78 (quintet, J=6.3 Hz, 2H), 0.88 (s, 9H), 0.00 (s, 6H); MS (APCI+)=206.1. Anal. Calcd./Found for C9H23NO2Si: C, 52.64/52.22; H, 11.29/10.94; N, 6.82/6.46.

Provenance & Evidence