Nitrogen → HCID 57250906, Verbindung

HRID 234727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234727
[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.N#N.FC(F)(F)S(O[Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])(=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:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])[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

5

Edukt 3

HCID 947NitrogenHCID 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 313-hydroxy-7-oxochol-5-en-24-oate (2) (5.02 g, 12.5 mmoles) and 2,6-1utidine (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 HCl, 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): δ0.67 (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 HCl
  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-e79937d60d984ae6b527a3f8319d44e9
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05595996

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