Triphenylphosphine → 3alpha-Azido-5alpha-pregnan-20-one

HRID 1829636

Reaktionsgleichung

Reaktionsgleichung von HRID 1829636
O[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]2C(=O)C)[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O:52][CH2:53][CH3:54])=O)=NC(OCC)=O.C1(P([N:69]=[N+:70]=[N-:71])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:69]([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:53](=[O:52])[CH3:54])[CH2:3]1)=[N+:70]=[N-:71]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 92787IsopregnanoloneHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Produkt 1

HCID 99460603alpha-Azido-5alpha-pregnan-20-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3β-hydroxy-5α-pregnan-20-one (60 mg, 0.19 mmol) in THF (2 mL) was treated with triphenylphosphine (100 mg, 0.38 mmol) and diethyl azo-dicarboxylate (0.03 mL, 0.19 mmol). To the resulting solution was added dropwise diphenylphosphoryl azide (0.04 mL, 0.19 mmol) and the mixture was stirred at RT for 24 h. Evaporation of the solvent in vacuo and purification of the residue using flash column chromatography using petroleum ether/ethyl acetate 90/10 as elution solvent afforded the compound named above.

Aufarbeitung

  1. customEvaporation of the solvent
  2. customin vacuo and purification of the residue
  3. washas elution solvent
  4. customafforded the compound

Quellen und Nachweise

ORD-Eintrag
ord-50ff6a499e1248a5b68789a496cc640e
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064116B2

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