Reaktion #86291

ord-56530e5dd603406890817f299bf356cb

Reaktionsgleichung

CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
methyl prednisolone 21-acetate
→
CC(=O)OCC(=O)C1(O)CCC2C3C[C@H](C)C4=CC(=O)C=C[C@]4(C)C3=CC[C@@]21C
title product
CC(=O)OCC(=O)C1(O)CCC2C3C[C@H](C)C4=CC(=O)C=C[C@]4(C)C3=CC[C@@]21C
2-((6S,10R,13S)-17-hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

Edukte

—
( 14 )
CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
methyl prednisolone 21-acetate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide
C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturcooled in an ice bath
  2. 2
    SonstigeSO2 is bubbled into methanesulfonyl chloride
  3. 3
    workup.ADDITIONthe mixture is added dropwise to the solution
  4. 4
    workup.ADDITIONcontaining the solution of methyl prednisolone 21-acetate

Vorschrift

(see Tetrahedron Letters, 2001, 42 (14): 2639-2642). Alternatively, methyl prednisolone 21-acetate is dissolved in a mixture of dimethylformamide and tetrahydrofuran and cooled in an ice bath. SO2 is bubbled into methanesulfonyl chloride and the mixture is added dropwise to the solution containing the solution of methyl prednisolone 21-acetate. The title product can then be isolated by standard aqueous workup.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434758B2uspto-grants-2016_09