Triphenylphosphine → HCID 16223168, Verbindung

HRID 1710884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710884
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([C:12]([O:14][CH3:15])=[O:13])[N:7]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:6][CH2:5]2.O[CH2:24][C:25]1[CH:26]=[C:27]([NH:31][C:32](=[O:34])[CH3:33])[CH:28]=[CH:29][CH:30]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:32]([NH:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([C:12]([O:14][CH3:15])=[O:13])[N:7]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:6][CH2:5]2)(=[O:34])[CH3:33]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 966393-Acetaminobenzyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 58858237(R)-2-tert-butyl 1-methyl 6-hydroxy-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate

Produkt 1

HCID 16223168HCID 16223168, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of (R)-2-tert-butyl 1-methyl 6-hydroxy-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate (99 mg, 0.32 mmol),N-(3-(hydroxymethyl)phenyl)acetamide (53 mg, 0.32 mmol)and PPh3 (92 mh, 0.35)in THF(2 mL) at 0° C. was added DEAD (60 μL, 0.38 mmol). The reaction mixture was warmed to room temperature and stirred overnight. It was concentrated and purified by preparative HPLC (Phenomenex 20×100 mm eluting with 0-100% MeOH/H2O (90% in H2O) gradient over 8 min with flow rate 25 mL/min) to yield (R)-2-tert-butyl 1-methyl 6-(3-acetamidobenzyloxy)-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate as a white solid(39 mg, 27%). HPLC retention time (Method C)=3.59 min. LC/MS (ESI) (M+H)+=477.26. 1H NMR (CDCl3, 400 MHz), 1:1 rotamers, δ ppm 1.47 (s, 5H), 1.49 (s, 4H), 2.71-2.98 (m, 2H), 3.60-3.84 (m, 2H), 3.70 (s, 3H), 5.03 (s, 2H), 5.37 (s, 0.5H), 5.53 (s, 0.5H), 6.74 (s, 1H), 6.82 (dd, J=8.59, 2.53 Hz, 1H), 7.15 (d, J=7.58 Hz, 1H), 7.29-7.39 (m, 2H), 7.46 (d, J=8.08 Hz, 1H), 7.58 (br. s., 1H).

Aufarbeitung

  1. concentrationIt was concentrated
  2. custompurified by preparative HPLC (Phenomenex 20×100 mm eluting with 0-100% MeOH/H2O (90% in H2O) gradient over 8 min with flow rate 25 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-b3d76201d7e54759b21652ebc3b4c948
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790745B2

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