p-Toluenesulfonic acid → 2beta-(4-Morpholinyl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol

HRID 2099863

反応式

HRID 2099863 の反応式
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C@@H:12]([OH:21])[C@@H:11]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:10]2)[CH2:7][CH2:6]3.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>>[N:44]1([C@H:2]2[CH2:19][C@@:18]3([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][C@H:11]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[C@@H:12]3[OH:21])[CH2:4][C@@H:3]2[OH:1])[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1

参加物

5

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 10340Sodium CarbonateHCID 160638722Alpha,3alpha-epoxy-16beta-(1-pyrrolidinyl)-5alpha-androstan-17beta-OL

生成物 1

HCID 160638732beta-(4-Morpholinyl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol

反応条件

温度
105 °C

実験手順

A suspension of 2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstan-17β-ol (1.80 Kg, 5.006 mol) in a mixture of morpholine (11.44 L) and purified water (1.144 L) was prepared at 20-24° C. and under N2 atmosphere. To the suspension was added p-toluenesulphonic acid (1.24 Kg, 6.508 mol) at 20-24° C. and under N2 atmosphere. The suspension was stirred in the darkness and heated to reflux (100-110° C.) for 40 h. After 40 h the reaction mixture was cooled to 20-24° C., and poured into a second vessel maintained at about 4° C. containing a 2% s solution of sodium carbonate (128 L), while stirred vigorously. The resulting suspension was stirred for 1 hour at about 4° C. The obtained solid was filtered off under vacuum, washed with cold purified water (100 L), and dried in a vacuum oven at about 40° C. for at least 48 hours, to give 2.07 Kg (4.49 mol) of a white solid. (89.7% molar yield and purity of 94.12% area by HPLC) m.p. 225° C.; [α]D20+82.00 (c=1.02 in CHCl3). The product could be used in the next stage without further purification.

後処理

  1. custompurified water (1.144 L)
  2. customwas prepared at 20-24° C. and under N2 atmosphere
  3. temperatureheated
  4. temperatureAfter 40 h the reaction mixture was cooled to 20-24° C.
  5. additionpoured into a second vessel
  6. temperaturemaintained at about 4° C.
  7. additioncontaining a 2%
  8. stirringwhile stirred vigorously
  9. stirringThe resulting suspension was stirred for 1 hour at about 4° C
  10. filtrationThe obtained solid was filtered off under vacuum
  11. washwashed
  12. customwith cold purified water (100 L)
  13. customdried in a vacuum oven at about 40° C. for at least 48 hours

出典と根拠

ORDレコード
ord-297b84df1cf647059c26317271800b20
出典データセット
uspto-grants-2009_08
特許番号
US07569687B2

関連ノート

読み込み中…