Diethyl Ether → 3alpha-Nicotinoyloxy-5alpha-pregnan-20-one

HRID 232804

Reaktionsgleichung

[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1.CCOCC>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:25]([O:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To 3α-hydroxy-5α-pregnan-20-one (464 mg, 318.5 g/m, 1.5 mmol) and 4-dimethylaminopyridine (DMAP, 195 mg, 122.17 g/m, 1.6 mmol) dissolved in 10 mL of dry pyridine was added nicotinoyl chloride hydrochloride (285 mg, 178.02 g/m, 1.6 mmol). The reaction mixture was heated at 90° C. for 5 hours and poured into 300 mL of ether. The organic layer was washed twice with saturated sodium bicarbonate, twice with water, dried over magnesium sulfate, and concentrated in vacuo to give the crude product. The crude material was filtered through a bed of silica gel using hexane/ethyl acetate (50:50) elution. The first two fractions gave the title compound (604 mg, 421 6/m, 1.43 mmol, 96%).

Aufarbeitung

washThe organic layer was washed twice with saturated sodium bicarbonate, twice with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customto give the crude product
filtrationThe crude material was filtered through a bed of silica gel
washhexane/ethyl acetate (50:50) elution

Quellen und Nachweise

ORD-Eintrag: ord-0d00213721f34e9290417906754dafe7
Quelldatensatz: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05591733

Verknüpfte Notizen

Wird geladen…