Hydrogen Peroxide → 17beta-Tetrahydropyranyloxy-4beta-hydroxy-5alpha-androstane

HRID 27332ノート

反応式

HRID 27332 の反応式
B.[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C:18](=[CH:19][CH2:20][CH2:21][CH2:22]1)[CH2:17][CH2:16]3.[OH-:28].[Na+].OO>O1CCCC1.O>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([C@@H:19]([OH:28])[CH2:20][CH2:21][CH2:22]1)[CH2:17][CH2:16]3

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 15341895HCID 15341895、化合物

生成物 1

HCID 1534189617beta-Tetrahydropyranyloxy-4beta-hydroxy-5alpha-androstane

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a cooled solution (0° C.) of 5 ml. of 1 M borane in tetrahydrofuran in 2.7 ml. of dry tetrahydrofuran was added 500 mg. (1.4 millimole) of the product of Step C. in 2.0 ml. of dry tetrahydrofuran. The clear solution was stirred for 1 hr. at room temperature and then cooled to 0° C. and treated with 5 ml. of 2.5 N sodium hydroxide followed by 4 ml. of 30% hydrogen peroxide. The solution was stirred for 1 hr. at room temperature, diluted with water and extracted with ethyl ether, washed with water, brine, dried and evaporated to an oily crystalline material. The product was washed with cold methanol and pumped dry to give 175 mg. of final product having a m.p. of 167°-170° C.

後処理

  1. customTo a cooled solution (0° C.) of 5 ml
  2. additiontreated with 5 ml
  3. stirringThe solution was stirred for 1 hr
  4. extractionextracted with ethyl ether
  5. washwashed with water, brine
  6. customdried
  7. customevaporated to an oily crystalline material
  8. washThe product was washed with cold methanol
  9. custompumped dry
  10. customto give 175 mg

出典と根拠

ORDレコード
ord-f7b4b13f31f1474b91baa4a400875309
出典データセット
uspto-grants-1980_09
特許番号
US04220775

反応ノート

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