Phosphoric Acid → Pyridyldithio-alcohol

3-Aminopropanol (0.76 ml, 10 mmol) was dissolved in a mixture of CH2Cl2 (5 ml) and 2-propanol (3 ml) and cooled in an ice bath. A solution of SPDP (1.23 g, 3.9 mmol) in CH2Cl2 (2 ml) was added dropwise in ca. 1 min. The mixture was stirred in the cooling bath for 1.25 h, and a 13% aqueous solution of NaH2PO4 (15 ml) and 85% H3PO4 (0.5 ml) were added. The products were extracted with ethyl acetate (2×30 ml), the organic layers were washed with 13% NaH2PO4, 15% KHCO3 and dried in vacuo. The crude compound 3 (1.14 g) was purified by flash-chromatography on silica-gel, elution with mixtures of CHCl3 and 2-propanol (100:0 to 100:7 by volume). Yield of pure compound 3 was 1.01 g (94%). TLC of compound 3 (CHCl3-2-propanol, 9:1): one spot, Rf ca. 0.3. 1H NMR of compound 3 (CDCl3), δ, ppm: 1.68 (quint., 6 Hz, 2H), 2.60 (t, 7 Hz, 2H), 3.05 (t, 7 Hz, 2H), 3.4 (br., 1H), 3.42 (q, 6 Hz, 2H), 3.62 (br., 2H), 6.99 (br., 1H), 7.10 (m, 1H), 7.58-7.65 (m, 1H).

1. temperaturecooled in an ice bath
2. extractionThe products were extracted with ethyl acetate (2×30 ml)
3. washthe organic layers were washed with 13% NaH2PO4, 15% KHCO3
4. customdried in vacuo
5. customThe crude compound 3 (1.14 g) was purified by flash-chromatography on silica-gel, elution with mixtures of CHCl3 and 2-propanol (100:0 to 100:7 by volume)

ORD 기록

ord-c8e64727156549869c1b4292a19e966d

출처 데이터셋

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08084435B2