The resolution of benzoyloscine / by Frank Tutin.

  • Tutin, Frank.
Date:
1910
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The resolution of benzoyloscine / by Frank Tutin. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

    3/8 (page 1793)
    CXCII.—The Resolution of Benzoyloseine. By Frank Tutin. The base oscine (scopoline), C8H1302N, formed by tbe hydrolysis of the alkaloid hyoscine (scopolamine), is generally acknowledged to bo closely related structurally to tropine, C8H15ON, although its constitution is not known. Tropine, which contains two similar asymmetric carbon atoms, has recently been examined from a stereochemical point of view by M. Barrowcliff and the present author (Trans., 1909, 95, 1966), and found to be an internally compensated compound. It was therefore considered of interest to investigate oscine in the same direction, particularly as the evidence so obtained might be of service in assigning a constitutional formula to this compound. Oscine was prepared from Z-hyoscine, and examined polari- metrically, when it was found to be optically inactive. As the amount of material prepared was not large, the base was converted into its benzoyl derivative before attempting its resolution, thereby increasing the size of the molecule. Moreover, the salts of benzoyl- oscine crystallise more readily than those of the original base. Benzoyloscine d-camphorsulphonate (m. p. 167—168°) was first prepared, but, although this salt was submitted to a prolonged fractional crystallisation, no evidence of resolution could be obtained. When, however, benzoyloscine d-bromocamphorsulphonate was fractionally crystallised, it was at once seen that a separation was being effected, and, after three fractionations, benzoyl-d-oseine d-bromocamphorsulphonate (m. p. 246°) was obtained in a state of purity. This salt had [a]D +51‘9° in aqueous solution, from which it is calculated that the basic ion has [o]D +10‘0°. The base obtained from this salt, when examined in 50 per cent, alcohol, had