Androstenedione → Androsta-3,5-dien-17-one, 3-(1-pyrrolidinyl)-

HRID 1439120

Reaktionsgleichung

Reaktionsgleichung von HRID 1439120
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=O)[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CO>[N:22]1([C:12]2[CH2:13][CH2:14][C@@:15]3([CH3:16])[C:10](=[CH:9][CH2:8][C@@H:7]4[C@@H:17]3[CH2:18][CH2:19][C@@:2]3([CH3:1])[C@H:6]4[CH2:5][CH2:4][C:3]3=[O:21])[CH:11]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Komponenten

4

Edukt 2

HCID 6128AndrostenedioneHCID 31268Pyrrolidine2×

Produkt 1

HCID 101900Androsta-3,5-dien-17-one, 3-(1-pyrrolidinyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 113.5 parts of crude androst-4-ene-3,17-dione in 427 parts of methanol is heated to just below reflux temperature. To the resulting stirred solution there is added 4.3 parts of pyrrolidine. After five minutes, more pyrrolidine is added at a steady rate so that 33.2 parts are added over a period of 25 minutes. The warm mixture is then stirred for an additional 15 minutes before it is cooled to 5°-10° C. The solid product which formed during the reaction is then separated by filtration and washed several times with methanol at 10° C. The solid is then dried to give 3-(1-pyrrolidinyl)androsta-3,5-dien-17-one melting at about 217°-220° C.

Aufarbeitung

  1. temperaturebelow reflux temperature
  2. additionare added over a period of 25 minutes
  3. stirringThe warm mixture is then stirred for an additional 15 minutes before it
  4. temperatureis cooled to 5°-10° C
  5. customThe solid product which formed during the reaction
  6. customis then separated by filtration
  7. washwashed several times with methanol at 10° C
  8. customThe solid is then dried

Quellen und Nachweise

ORD-Eintrag
ord-49b1a5086f864c36abe763789faaf87c
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04057542

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