Methyl 2-acetoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)acrylate → (R)-Methyl 2-acetoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)propanoate

HRID 501937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501937
[C:1]([O:4][C:5](=[CH:10][C:11]1[CH:19]=[C:18]([CH3:20])[C:17]2[C:13](=[CH:14][N:15]([CH2:21][O:22][CH3:23])[N:16]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]>ClCCl>[C:1]([O:4][C@H:5]([CH2:10][C:11]1[CH:19]=[C:18]([CH3:20])[C:17]2[C:13](=[CH:14][N:15]([CH2:21][O:22][CH3:23])[N:16]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

Komponenten

3

Edukt 1

HCID 68460956Methyl 2-acetoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)acrylate

Produkt 1

HCID 57794608(R)-Methyl 2-acetoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-acetoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)acrylate (2.80 g, 8.8 mmol) in dichloromethane (20 mL) was degassed by passing a stream of nitrogen through the solution. To this solution was quickly added (−)-1,2-bis((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium (I) trifluoromethylsulfonate (100 mg, 0.016 equiv) as a solid. The reaction was placed under a hydrogen atmosphere (55 psi) and shaken overnight. The reaction was concentrated and purified by column chromatography (50% ethyl acetate/hexanes) to give 2.74 g (97%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 2.08 (s, 3H), 2.61 (s, 3H), 3.11 (dd, J=14.3, 8.9, 1H), 3.20 (dd, J=14.3, 4.6, 1H), 3.39 (s, 3H), 3.72 (s, 3H), 5.26 (dd, J=8.9, 4.6, 1H), 5.68 (s, 2H), 6.93 (s, 1H), 7.33 (s, 1H), 8.02 (s, 1H).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography (50% ethyl acetate/hexanes)
  3. customto give 2.74 g (97%) as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-43f44f35ff91402ea0a8c6ea2ae2d993
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772244B2

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