2062. Chirald

Nomenclature

CAS number: 38345-66-3
(αS)-α-[(1R)-2-(Dimethylamino)-1-methylethyl]-α-phenylbenzeneethanol; (+)-oxyphene; (2S,3R)-(+)-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol; Darvon alcohol.
C19H25NO; mol wt 283.41.
C 80.52%, H 8.89%, N 4.94%, O 5.65%.

Description and references

Asymmetric reducing agent. Prepn of racemate: W. G. Stoll et al., Helv. Chim. Acta 33, 1194 (1950). Resolution of enantionmers: A. Pohland, H. R. Sullivan, J. Am. Chem. Soc. 77, 3400 (1955). Asymmetric synthesis: T. J. Erickson, J. Org. Chem. 51, 934 (1986). HPLC determn as an impurity in dextropropoxyphene, q.v.: S. Kryger, P. Helboe, J. Chromatogr. 539, 186 (1991). Use as an enantioselective reducing agent: M. N. Nefedova et al., J. Organomet. Chem. 425, 125 (1992); D. R. Williams et al., Tetrahedron Lett. 41, 9397 (2000).

Chemical structure

Properties

mp 55-57°. bp0.1 mm 138-139°. Flash point: >230°F . [α]21 +8.2° (c = 10 in ethanol).

Note

Also referred to in the literature as Mosher's reagent, q.v.

Use

Reducing reagent in organic synthesis.