Реакция #1702047

ord-4899f269dcfd4f3c848bddab5b589af2

Уравнение реакции

COC(=O)c1ccc([C@H]2CCC(=O)C2)cc1
(S)-4-(3-Oxo-cyclopentyl)-benzoic acid methyl ester
O=C1CC[C@H](c2ccc(C(=O)O)cc2)C1
title compound
Выход 100.3%
O=C1CC[C@H](c2ccc(C(=O)O)cc2)C1
4-[(1S)-3-Oxocyclopentyl]benzoic acid
Выход 100.3%

Реагенты

Нет

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеThen the MeOH was evaporated
  2. 2
    workup.ADDITIONthe reaction mixture diluted with water
  3. 3
    Экстракцияextracted with DCM
  4. 4
    СушкаDried over Na2SO4
  5. 5
    Концентрированиеconcentrated in vacuo

Методика

(S)-4-(3-Oxo-cyclopentyl)-benzoic acid methyl ester (preparation 19) (10.2 mmol, 2.25 g) was taken up in MeOH (6 mL) and NaOH (2N, 6 mL), the reaction mixture stirred at r.t. for 2 h. Then the MeOH was evaporated and the reaction mixture diluted with water, then neutralized with HCl (2N) to pH 5 and extracted with DCM. Dried over Na2SO4 and concentrated in vacuo to yield the title compound (2.09 g, 99%). 1H NMR (300 MHz, DMSO) δ 12.83 (br s, 1H), 7.94-7.84 (m, 2H), 7.45 (d, 2H), 3.55-3.39 (m, 1H), 2.65-2.52 (m, 1H), 2.41-2.21 (m, 4H), 2.03-1.84 (m, 1H).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08765676B2uspto-grants-2014_07