Formaldehyde → 17beta-Hydroxy-17alpha-methyl-6-methyleneandrosta-4,15-diene-3-one

HRID 274309노트

반응식

HRID 274309 반응식
[OH:1][C@@:2]1([CH3:22])[CH:7]=[CH:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.C=O.F[C:26](F)(F)C([O-])=O.C[NH2+]C1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[OH:1][C@@:2]1([CH3:22])[CH:7]=[CH:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[C:10](=[CH2:26])[CH2:9]3

참가 물질

6

반응물 3

HCID 712FormaldehydeHCID 2724109N-Methylanilinium trifluoroacetateHCID 1567913617beta-Hydroxy-17alpha-methylandrosta-4,15-dien-3-one

생성물 1

HCID 1567914917beta-Hydroxy-17alpha-methyl-6-methyleneandrosta-4,15-diene-3-one수율 43.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

500 mg of 17β-hydroxy-17α-methylandrosta-4,15-dien-3-one in 8.3 ml of tetrahydrofuran is stirred at 60° C. under argon with 348 mg of paraformaldehyde and 2.2 g of N-methylanilinium trifluoroacetate. After 3.5 hours, the mixture is diluted with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated under vacuum. After the crude product has been chromatographed on silica gel with a pentane-diethyl ether gradient, 226 mg of 17β-hydroxy-17α-methyl-6-methyleneandrosta-4,15-dien-3-one is obtained, mp 162° C. (from isopropyl ether).

후처리

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customAfter the crude product has been chromatographed on silica gel with a pentane-diethyl ether gradient

출처 및 근거

ORD 기록
ord-b8251a7cb1e8404081cc15d107ca2282
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389624

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