Réaction #1005585

ord-7503150db3f24ed69c50a2ca3de1ccfc

Équation de réaction

CCOC(C=[N+]=[N-])OCC
2,2-diethoxy-1-diazoethane
CCOC(CNC(N)=O)OCC
N-2,2-diethoxyethyl urea
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1C[C@@H](O)[C@]2(O)C(=O)CO
11β,16α,17,21-Tetrahydroxypregn-4-ene-3,20-dione
→
CCOC(CO[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO)OCC
title compound
CCOC(CO[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO)OCC
16α-(2,2-Diethoxyethoxy)-11β,17,21-trihydroxypregn-4-ene-3,20-dione

Réactifs

CCOC(C=[N+]=[N-])OCC
2,2-diethoxy-1-diazoethane
CCOC(CNC(N)=O)OCC
N-2,2-diethoxyethyl urea
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1C[C@@H](O)[C@]2(O)C(=O)CO
11β,16α,17,21-Tetrahydroxypregn-4-ene-3,20-dione

Réactifs

Aucun

Solvants

CCCCC.CCOCC
ether pentane
CO
methanol

Conditions de réaction

Température
0°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe solvent is removed in vacuo
  2. 2
    Autrethe residue is recrystallized from methanol

Mode opératoire

A solution of 2,2-diethoxy-1-diazoethane (prepared from 0.0935 mole of N-2,2-diethoxyethyl urea by the method of W. Kirmse and B. Buschhoff, Chem. Ber., 100, 1491 (1967)) in 300 ml of 3:2 ether pentane is diluted with 100 ml of methanol and cooled to 0°C. 11β,16α,17,21-Tetrahydroxypregn-4-ene-3,20-dione, 16,17-cycloborate is added in portions until nitrogen evolution ceases. The solvent is removed in vacuo and the residue is recrystallized from methanol to yield the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US03971773uspto-grants-1976_07