Реакция #657252

ord-bf5005f846794a4ab660f2c1eb1fa35e

Уравнение реакции

O=Cc1cc(Br)cc2c1OCC2
20
O=Cc1cc(Br)cc2c1OCC2
5-Bromo-2,3-dihydrobenzofuran-7-carbaldehyde
CN[C@@H](C)[C@@H](O)c1ccccc1
(1S,2S) pseudoephedrine
C[C@H]1[C@H](c2ccccc2)OC(c2cc(Br)cc3c2OCC3)N1C
21
Выход 79.0%
C[C@H]1[C@H](c2ccccc2)OC(c2cc(Br)cc3c2OCC3)N1C
(4S,5S)-2-(5-bromo-2,3-dihydrobenzofuran-7-yl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine
Выход 79.0%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеSolvent removal
  2. 2
    Другоеyielded yellow crystals which
  3. 3
    Другоеwere recrystallized from a minimum of hot hexanes

Методика

A sample of 20 (650 mg, 2.9 mmol) and (1S,2S) pseudoephedrine (500 mg, 3.0 mmol) in 40 mL of benzene was refluxed overnight using a Dean-Stark trap. Solvent removal yielded yellow crystals which were recrystallized from a minimum of hot hexanes to give white crystals of 21 (841 mg, 79%), mp=83.5-85.5° C.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09023317B2uspto-grants-2015_05