TacroliMus Methyl Acryl Aldehyde synthesis

Yield: 60%

Reaction Conditions:

with sodium t-butanolate in tert-butyl alcohol at 65; for 1.5 h;

Steps:

Reaction of tacrolimus with sodium t-butoxide
Tacrolimus (1, 250 mg, 0.30 mmol) was added to sodium t-butoxide (61 mg, 0.64 mmol) in t-butanol (25 ml), and the solution was stirred at 65 °C for 1.5 h.
The reaction mixture was quenched with water (40 ml) and extracted with EtOAc (3 * 25 ml).
The combined organic layer was washed with brine (15 ml), dried over Na₂SO₄, filtered, and concentrated in vacuo.
The product was recrystallized from heptane to give 8 (36 mg, 60%) as colorless crystals.

References:

Skytte, Dorthe M.;Jaroszewski, Jerzy W.;Johansen, Kenneth T.;Hansen, Steen Honore;Hansen, Liselotte;Nielsen, Peter G.;Frydenvang, Karla [European Journal of Pharmaceutical Sciences,2013,vol. 48,# 3,p. 514 - 522]