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m-Chloroperbenzoic acid → tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(1-oxidopyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate

HRID 1911845
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1911845
[Si:1]([O:8][C@H:9]([C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=2)[N:11]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:47])C=1>C(Cl)Cl>[Si:1]([O:8][C@H:9]([C:33]1[CH:34]=[N+:35]([O-:47])[CH:36]=[CH:37][CH:38]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=2)[N:11]1[C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]
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Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 86666749Tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate

Produkt 1

HCID 86670463tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(1-oxidopyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate (1.15 g, 2.127 mmol) in DCM (22 mL) was cooled to 0° C. and m-CPBA (0.953 g, 4.25 mmol) was added. The reaction was warmed to room temperature. After 2 hours the reaction was quenched with aqueous sodium bisulfite (20 mL). The reaction was then diluted with EtOAc (150 mL) and washed vigorously with aqueous sodium bisulfite (3×40 mL). The organics were washed with brine (2×40 mL), saturated aqueous NaHCO3 (3×40 mL) and then brine (2×40 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(1-oxidopyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate (1.18 g, 100%). LC-MS=557.2 (M+1)+.

Aufarbeitung

  1. customAfter 2 hours the reaction was quenched with aqueous sodium bisulfite (20 mL)
  2. additionThe reaction was then diluted with EtOAc (150 mL)
  3. washwashed vigorously with aqueous sodium bisulfite (3×40 mL)
  4. washThe organics were washed with brine (2×40 mL), saturated aqueous NaHCO3 (3×40 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c4071116022f41169a3276180728ed7e
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08604038B2

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