Triphenylphosphine → ethyl 5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate

HRID 606581

Reaktionsgleichung

Reaktionsgleichung von HRID 606581
C1(P([C:14]2[CH:19]=[CH:18]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:34][C:35]1[CH:36]=[CH:37][C:38]2[O:42][C:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:40][C:39]=2[CH:48]=1.[C:49]([N:56]1CC[O:59][CH2:58][CH:57]1C(O)=O)([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50]>ClCCl>[C:49]([N:56]1[CH2:57][CH2:58][O:59][CH:19]([CH2:14][O:34][C:35]2[CH:36]=[CH:37][C:38]3[O:42][C:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:40][C:39]=3[CH:48]=2)[CH2:18]1)([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acidHCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylate

Produkt 1

HCID 67046596ethyl 5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triphenyl phosphine polymer bound (8.96 mmol) was suspended in anhydrous dichloromethane (20 ml) then diisopropyl azodicarboxylate (7.76 mmol) was added and the mixture was stirred for 15 minutes at room temperature. Then ethyl 5-hydroxybenzofuran carboxylate (5.97 mmol) was added over 5 minutes followed by the addition of 4-N-boc-3-morpholinecarboxylic acid (5.97 mmol) over 5 minutes too. The mixture was stirred at room temperature over night. The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate: m/z=406 in MS ES+, as clear oil.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature over night
  2. customThe solvent was evaporated under vacuo
  3. customthe residue purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7ebb8d9bffd14e4a8362df707733df37
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915300B2

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