Water → HCID 131719763, Verbindung

HRID 232760

Reaktionsgleichung

Reaktionsgleichung von HRID 232760
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C@H:11]3[CH2:28][C@@:27]4([CH3:29])[C@@H:14]([CH2:15][CH2:16][C@@H:17]5[C@@H:26]4[CH2:25][CH2:24][C@@:22]4([CH3:23])[C@H:18]5[CH2:19][C@H:20]([N:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[C@@H:21]4[OH:30])[CH2:13][C@@H:12]3[OH:36])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:37](Cl)(=[O:39])[CH3:38].O>C(Cl)Cl.C(N(CC)CC)C>[O:4]1[C:5]2([CH2:6][CH2:7][N:8]([C@H:11]3[CH2:28][C@@:27]4([CH3:29])[C@@H:14]([CH2:15][CH2:16][C@@H:17]5[C@@H:26]4[CH2:25][CH2:24][C@@:22]4([CH3:23])[C@H:18]5[CH2:19][C@H:20]([N:31]5[CH2:32][CH2:33][CH2:34][CH2:35]5)[C@@H:21]4[OH:30])[CH2:13][C@@H:12]3[OH:36])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1.[CH3:38][C:37]([CH2:6][C:5]([OH:4])=[O:1])=[O:39]

Komponenten

6

Edukt 3

HCID 962WaterHCID 6367Acetyl chloride2×HCID 228685452beta-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol

Produkt 1

HCID 131719763HCID 131719763, VerbindungAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution containing 10 g of 2β-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-16β-(1-pyrrolidinyl)-5α-androstane-3α,17β-diol in 50 ml of methylene chloride, 7 ml of triethylamine are added and the solution is cooled to 0° C. To this solution 4.4 ml of acetyl chloride are dropwise added while cooling and stirring at such a rate that the temperature remains below 10° C. After termination of the addition the cooling is stopped and the mixture is allowed to warm to room temperature. The complete reaction requires about 16 hours. Thereafter, the excess of acetyl chloride is decomposed by adding water and the methylene chloride solution is washed with aqueous sodium hydroxide solution and then with water until neutral. The methylene chloride phase is dried, evaporated and the residue is purified on a silica gel column to yield 9 g (77.1%) of the title product as a foam.

Aufarbeitung

  1. additionare added
  2. temperaturewhile cooling
  3. customremains below 10° C
  4. additionAfter termination of the addition the cooling
  5. temperatureto warm to room temperature
  6. customThe complete reaction
  7. washthe methylene chloride solution is washed with aqueous sodium hydroxide solution
  8. dry with materialThe methylene chloride phase is dried
  9. customevaporated
  10. customthe residue is purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-8fd1eca4d95b4988b51786056f8a5d40
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591735

Verknüpfte Notizen

Wird geladen…