Morpholine → (1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-6'-(morpholinomethyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

HRID 1716967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716967
CC1C=CC(S(O[CH2:12][C@H:13]2[O:18][C@@:17]3([C:26]4[C:21](=[CH:22][C:23]([Cl:36])=[C:24]([CH2:27][C:28]5[CH:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][CH:29]=5)[CH:25]=4)[CH2:20][O:19]3)[C@H:16]([OH:37])[C@@H:15]([OH:38])[C@@H:14]2[OH:39])(=O)=O)=CC=1.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>>[Cl:36][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][C:24]=1[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][CH3:35])=[CH:32][CH:33]=1)[C@:17]1([C@H:16]([OH:37])[C@@H:15]([OH:38])[C@H:14]([OH:39])[C@@H:13]([CH2:12][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[O:18]1)[O:19][CH2:20]2

Komponenten

3

Edukt 2

HCID 8083MorpholineHCID 59013460((1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-3',4',5'-trihydroxy-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-6'-yl)methyl 4-methylbenzenesulfonate

Produkt 1

HCID 59013464(1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-6'-(morpholinomethyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

Versuchsvorschrift

((1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-3′,4′,5′-trihydroxy-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-6′-yl)methyl 4-methylbenzenesulfonate (20 mg, 0.034 mmol) was dissolved in 1 mL of morpholine. Then the solution was allowed to reflux overnight. Concentration under reduced pressure provided the crude product, which was purified by preparative TLC to give 15 mg of title compound. 1H NMR (CD3OD, 400 MHz) δ 7.37 (s, 1H), 7.18 (s, 1H), 7.11 (d, J=8.0 Hz, 2H), 7.09 (d, J=8.8 Hz, 2H), 5.17 (d, J=13.2 Hz, 1H), 5.11 (d, J=13.2 Hz, 1H), 4.65-4.60 (m, 2H), 4.18-4.00 (m, 4H), 3.82-3.50 (m, 7H), 3.31-3.25 (m, 1H), 3.08-2.99 (m, 2H), 2.61 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H); MS ESI (m/z) 490 (M+1)+, calc. 489.

Aufarbeitung

  1. temperatureto reflux overnight
  2. concentrationConcentration under reduced pressure
  3. customprovided the crude product, which
  4. customwas purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-40263ae52315448cafee47630e09d8f3
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803778B2

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