HCID 59189493, Verbindung → HCID 86639081, Verbindung

HRID 456328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456328
[C@:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10](Cl)=[O:11].[I:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([OH:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[C:17]([N+:27]([O-:29])=[O:28])[CH:16]=1>CN(C1C=CN=CC=1)C.ClCCl>[C@:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10]([O:26][CH:21]([C:18]1[CH:19]=[CH:20][C:15]([I:14])=[CH:16][C:17]=1[N+:27]([O-:29])=[O:28])[C:22]([CH3:24])([CH3:25])[CH3:23])=[O:11]

Komponenten

5

Edukt 2

HCID 59189493HCID 59189493, VerbindungHCID 71432218(1s)-Camphanoyl chloride

Produkt 1

HCID 86639081HCID 86639081, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, (1S)-camphanic acid chloride (1.68 g, 7.77 mmol) was added to a solution of (RS)-1-(4-iodo-2-nitrophenyl)-2,2-dimethyl-1-propanol (2.17 g, 6.47 mmol) and DMAP (1.18 g, 9.7 mmol) in anhydrous dichloromethane (50 mL). The mixture was stirred overnight at room temperature and then washed with saturated NaHCO3 solution (60 mL) and water (60 mL). The organic phase was dried over Na2SO4, concentrated in vacuo and purified by silica gel column chromatography to yield (RS)-1-(4-iodo-2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (2.94 g, 88%, 1:1 mixture of diastereomers) as a white solid. 1H NMR (400 MHz, CDCl3) for diastereomers: δ 8.23 (m, 1 H, Ph-H), 7.90 (m, 1 H, Ph-H), 7.31 (m, 1 H, Ph-H), 6.56 and 6.51 (2 s, 1 H, Ph-CH), 2.38 (m, 1H), 2.07-1.9 (m, 2H), 1.69 (m, 1H), 1.13, 1.11, 1.07, 1.04, 1.02, 0.87 (6 s, 9 H, CH3×3), 0.96 (s, 9 H, (CH3)3C).

Aufarbeitung

  1. washwashed with saturated NaHCO3 solution (60 mL) and water (60 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-54f98c23035c4f86a21c9236daa5d142
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497360B2

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