Nitrogen → HCID 57250906, Verbindung

HRID 1456007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1456007
[OH:1][C@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:4](=[CH:5][C:6](=[O:29])[C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.N1C(C)=CC=CC=1C.N#N.FC(F)(F)S(O[Si:46]([CH:53]([CH3:55])[CH3:54])([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48])(=O)=O>C(Cl)Cl>[O:29]=[C:6]1[CH:5]=[C:4]2[C@:24]([CH3:27])([CH2:25][CH2:26][C@H:2]([O:1][Si:46]([CH:53]([CH3:55])[CH3:54])([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48])[CH2:3]2)[C@@H:23]2[C@@H:7]1[C@H:8]1[C@:20]([CH3:28])([CH2:21][CH2:22]2)[C@@H:11]([C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:9]1

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 23250094Methyl (3β)-3-hydroxy-7-oxochol-5-en-24-oate

Produkt 1

HCID 57250906HCID 57250906, VerbindungAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 3β-hydroxy-7-oxochol-5-en-24-oate (2) (5.02 g, 12.5 mmoles) and 2,6-lutidine (3.32 ml, 28.5 mmoles) in CH2Cl2 (23 ml) cooled in an ice bath in a N2 atmosphere was added dropwise with magnetic stirring triisopropylsilyl trifluoromethanesulfonate (4.56 g, 17 mmoles). After 2 hrs, the reaction was diluted with CH2Cl2 (150 ml). It was then washed with cold 2N HCI, washed twice with H2O and then with saturated brine before drying with MgSO4. Evaporation in vacuo and purification of the residue by flash chromatography on silica gel with hexane-EtOAc (10:1) gave 5.88 g of 3 as a colorless syrup. NMR (CDCl3): δ 0.67 (s, 3H, 18-Me); 0.93 (d, 3H, 20-Me); 1.06 (s, 18H, TIPS Me); 1.19 (s, 3H, 19-Me); 3.66 (s, 3H, CO2Me); 3.68 (m, 1H, 3-H); 5.66 (s, 1H, 6-H).

Aufarbeitung

  1. additionwas added dropwise
  2. washIt was then washed with cold 2N HCI
  3. washwashed twice with H2O
  4. dry with materialwith saturated brine before drying with MgSO4
  5. customEvaporation
  6. customin vacuo and purification of the residue by flash chromatography on silica gel with hexane-EtOAc (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-a51b04f147f54a7ea17556147262193a
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843953

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