Tributylphosphine → Methyl 3-{5-[3-(benzyloxycarbonylamino)propoxy]-indolyl}propanoate

HRID 23985

Reaktionsgleichung

Reaktionsgleichung von HRID 23985
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[OH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:23]2.[CH2:35]([O:42][C:43]([NH:45][CH2:46][CH2:47][CH2:48]O)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[CH2:35]([O:42][C:43]([NH:45][CH2:46][CH2:47][CH2:48][O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:23]2)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 562256Benzyl N-(3-hydroxypropyl)carbamateHCID 22570384methyl 3-(5-hydroxy-1H-indol-2-yl)propanoate

Produkt 1

HCID 22570338Methyl 3-{5-[3-(benzyloxycarbonylamino)propoxy]-indolyl}propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1,1′-(Azodicarbonyl)dipiperidine (370 mg, 1.5 mmol) was added to the solution of methyl 3-(5-hydroxyindolyl)propanoate (220 mg, 1.0 mmol), as prepared in step g of Example 5, 3-(benzyloxycarbonylamino)propanol (230 mg, 1.1 mmol) and tri-n-butylphosphine (305 mg, 1.5 mmol) in tetrahydrofuran (20 mL). After stirring at ambient temperature overnight, the reaction mixture was concentrated and the residue was purified by flash column chromatography on silica gel (0-2% ethyl acetate in methylene chloride) to give the title compound as an off white solid (310 mg, 76%). 1H-NMR (400 MHz, CDCl3) δ 7.35 (m, 5H), 7.22 (d, J=8.9 Hz, 1H), 7.09 (d, J=3.1 Hz, 1H), 7.07 (d, J=2.1 Hz, 1H), 6.86 (dd, J=8.8, 2.4 Hz, 1H), 6.38 (d, J=2.9 Hz, 1H), 5.11 (br s, 3H), 4.41 (t, J=6.8 Hz, 2H), 4.07 (t, J=5.9 Hz, 2H), 3.66 (s, 3H), 3.44 (q, J=6.3 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 2.02 (m, 2H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel (0-2% ethyl acetate in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-b7e30da35c9f479082ec3a09dcec3b98
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855722B2

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