tert-Butyl acetate → HCID 91478440, Verbindung

HRID 1818632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818632
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH3:12].[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]([C:36](OCC)=[O:37])=[CH:23]2>C1COCC1>[CH2:29]([N:25]1[C:26]2[C:22](=[CH:21][C:20]([Cl:19])=[CH:28][CH:27]=2)[CH:23]=[C:24]1[C:36](=[O:37])[CH2:12][C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Komponenten

5

Edukt 3

HCID 10908tert-Butyl acetateHCID 2733832Lithium HexamethyldisilazideHCID 13295699Ethyl 1-benzyl-5-chloroindole-2-carboxylate

Produkt 1

HCID 91478440HCID 91478440, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled (−78° C.) solution of LHMDS (38 mL, 1.0 M in THF, 38 mmol) was added tert-butyl acetate (5.2 mL, 38.3 mmol). After 30 min, a solution of the title compound of Example 12 Step A (4.00 g, 12.8 mmol) in THF (10 mL) was added, and the mixture was held at −78° C. for 50 min, whereupon it was placed in a 0° C. bath. After 2 h, the reaction mixture was quenched by addition of sat. aq. NH4Cl, and the aqueous phase was extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20%, then 20-100% EtOAc in hexanes) provided the title compound: LCMS B, tr=2.70 min, m/z 328.1 [M−tBu+H]+; 1H NMR (500 MHz, CDCl3) δ 7.70 (s, 1H), 7.31 (s, 1H), 7.29-7.18 (m, 5H), 7.02 (d, J=7.0 Hz, 2H), 5.84 (s, 2H), 3.86 (s, 2H), 1.40 (s, 9H).

Aufarbeitung

  1. waitthe mixture was held at −78° C. for 50 min, whereupon it
  2. customwas placed in a 0° C.
  3. waitAfter 2 h
  4. customthe reaction mixture was quenched by addition of sat. aq. NH4Cl
  5. extractionthe aqueous phase was extracted with EtOAc
  6. dry with materialThe organic phase was dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel (0 to 20%

Quellen und Nachweise

ORD-Eintrag
ord-a2acdc97886144aabd15a941622e6f76
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598398B2

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