Pyridine → 7-Methyl-14,15-methyleneestr-4-en-3-one

HRID 49414노트

반응식

HRID 49414 반응식
OC[C@@H:3]1[CH2:8][C@H:7]2[CH2:9][C@@:6]32[C@H:10]2[C@H:19]([CH2:20][CH2:21][C@:4]13[CH3:5])[C@@H:18]1[C:13](=[CH:14][C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][C@H:11]2[CH3:23].N1C=CC=CC=1.C(OC(=O)C)(=O)C>O1CCCC1>[CH3:23][CH:11]1[CH2:12][C:13]2[C@H:18]([CH2:17][CH2:16][C:15](=[O:22])[CH:14]=2)[C@@H:19]2[C@@H:10]1[C@:6]13[CH2:9][CH:7]1[CH2:8][CH2:3][C@:4]3([CH2:21][CH2:20]2)[CH3:5]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 9796915(7alpha,14beta,15beta,17alpha)-17-(Hydroxymethyl)-7-methyl-14,15-methyleneestr-4-en-3-one

생성물 1

HCID 701471477-Methyl-14,15-methyleneestr-4-en-3-one수율 121.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (7α,14β,15β,17α)-17-(hydroxymethyl)-7-methyl-14,15-methyleneestr-4-en-3-one (Example 1, 0.20 g) in a mixture of dry pyridine (1.76 ml) and dry tetrahydrofuran (8.8 ml) was treated with acetic anhydride (1.06 ml). The mixture was stirred at room temperature overnight and then quenched with water. After 1 h stirring the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (7α,14β,15β,17α)17-[(acetyloxy)methyl)]-7-methyl-14,15-methyleneestr-4-en-3-one (0.22 g). 1H NMR (CDCl3) δ5.80 (t, 1H, J=2.8 Hz), 4.05 (dd, part A of AB system, 1H, J=11.0 and 6.3 Hz), 3.95 (dd, part B of AB system, 1H, J=11.0 and 7.1 Hz), 2.03 (s, 3H), 1.08 (s, 3H),. 0.62 (d, 3H, J=7.1 Hz), 0.48 (dd, 1H, J=8.3 and 5.1 Hz), 0.27 (dd, 1H, J=5.1 and 3.5 Hz).

후처리

  1. customquenched with water
  2. stirringAfter 1 h stirring the product
  3. extractionwas extracted into ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6067c95a42754a5ab37fe2b3f10db854
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706700B2

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