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

HRID 27332노트

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HRID 27332 반응식
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

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 15341895HCID 15341895, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f7b4b13f31f1474b91baa4a400875309
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220775

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