Hydracrylonitrile → HCID 19982451, compound

Diisopropylamino phosphorodichloridite (made in accordance with the procedure set forth in Takeo, Shimidzu, et al. Nucleic Acid Research Symposium Series No. 12,55-58 (1983)) (14.2g, 70.0 mmol) was added to a magnetically stirred solution of tetrahydrofuran (100 ml), diisopropylethylamine (36.6 ml, 210 mmol) and 3-hydroxypropionitrile (9.6 ml, 140 mmol) at 0° C. After 4 hours, the mixture was warmed to room temperature and stirred for an additional 2 hours. The hydrochloride salt was removed from the reaction mixture by filtration through a scintered glass funnel. The resulting filtrate was recovered, diluted 1/1 with ethyl acetate, and washed with three 100 ml portions of 5% NaHCO3. The organic portion was then dried over Na and evaporated to yield 17.7g of crude product as a yellow oil. The oil was dissolved in a mixture of dichloromethane/hexane/triethylamine (6/4/1 v/v/v) (50 ml) and applied to a column of silica gel (175 g) which had been equilibrated with the same solvent mixture. The column was eluted with the solvent mixture and fractions (20 ml) were collected. Fractions which contained the desired product were identified as bis-(2-cyanoethoxy)-N,N-diisopropylaminomethoxyphosphine (hereinafter referred to as Compound II) represented by formula set forth below: ##STR5## wherein i-Pr is isopropyl. (Rf=0.60 silica gel TLC developed in ethyl acetate/triethylamine 9/1). Fractions containing Component II were pooled, evaporated, and then coevaporated with toluene (3×5 ml) to yield the desired product as a colorless oil (11.1 g, 58.7%)31 p NMR=-146.75 ppm, relative to trimethylphosphate in CH2Cl2.

1. customThe hydrochloride salt was removed from the reaction mixture by filtration through a scintered glass funnel
2. customThe resulting filtrate was recovered
3. additiondiluted 1/1 with ethyl acetate
4. washwashed with three 100 ml portions of 5% NaHCO3
5. customThe organic portion was then dried over Na
6. customevaporated
7. customto yield 17.7g of crude product as a yellow oil
8. washThe column was eluted with the solvent mixture and fractions (20 ml)
9. customwere collected
10. additionFractions containing Component II
11. customevaporated

ORD record

ord-1283b423021e4dd78cc7f376041dc2dc

Source dataset

uspto-grants-1991_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05071974