Hydrochloric Acid → (1R,2R)-Methyl 2-(4-bromobenzoyl)cyclopentanecarboxylate

HRID 9547

Reaktionsgleichung

Reaktionsgleichung von HRID 9547
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([OH:15])=[O:14])=[O:7])=[CH:4][CH:3]=1.[CH3:18]OC(OC)(C)C.Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([O:15][CH3:18])=[O:14])=[O:7])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 64952,2-DimethoxypropaneHCID 23549251trans-2-(4-Bromobenzoyl)cyclopentanecarboxylic acid

Produkt 1

HCID 58681296(1R,2R)-Methyl 2-(4-bromobenzoyl)cyclopentanecarboxylateAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of trans-2-(4-bromobenzoyl)cyclopentanecarboxylic acid (2.0 g, 6.26 mmol) in MeOH (70 mL) was added 2,2-dimethoxypropane (1.63 g, 15.65 mmol) and HCl (4.0 M in dioxane) (1.0 mL). The resulting solution was stirred at 40° C. overnight and then evaporated to dryness. The resulting residue was purified by flash chromatography (Biotage Flash 40M) using 7 to 11% ethyl acetate in hexanes to afford methyl trans-2-(4-bromobenzoyl)cyclopentanecarboxylate (1.62 g, 83%). 1H NMR (400 MHz, CD2Cl2) δ 1.70–1.95 (m, 4H), 2.08–2.21 (m, 2H), 3.40 (m, 1H), 3.64 (s, 3H), 4.04 (m, 1H), 7.64 (m, 2H), 7.86 (m, 2H).

Aufarbeitung

  1. customevaporated to dryness
  2. customThe resulting residue was purified by flash chromatography (Biotage Flash 40M)

Quellen und Nachweise

ORD-Eintrag
ord-9bcf2b9ca09445f5b276604eaf8986b6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091228B2

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