Triethylamine → 16-Methylene-17-hydroxypregna-1,4,9(11)-triene-3,20-dione

HRID 1285316노트

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HRID 1285316 반응식
C[O:2]P(OC)OC.C(N(CC)CC)C.C1(S([CH2:23][C:24]2[C@@H:25]([C@:29]3([CH3:46])[C@@H:42]([CH:43]=2)[C@H:41]2[C:32]([C@:33]4([CH3:45])[C:38]([CH2:39][CH2:40]2)=[CH:37][C:36](=[O:44])[CH:35]=[CH:34]4)=[CH:31][CH2:30]3)[C:26](=[O:28])[CH3:27])=O)C=CC=CC=1>C1(C)C=CC=CC=1.CO>[OH:2][C@:25]1([C@:29]2([CH3:46])[C@H:42]([C@H:41]3[C:32](=[CH:31][CH2:30]2)[C@:33]2([CH3:45])[C:38](=[CH:37][C:36](=[O:44])[CH:35]=[CH:34]2)[CH2:39][CH2:40]3)[CH2:43][C:24]1=[CH2:23])[C:26](=[O:28])[CH3:27]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 8472Trimethyl phosphiteHCID 18601425HCID 18601425, 화합물

생성물 1

HCID 308215016-Methylene-17-hydroxypregna-1,4,9(11)-triene-3,20-dione

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

Trimethylphosphite (0.3 ml) and triethylamine (0.3 ml) are added to a solution of 16(phenylsulfinylmethyl)pregn-1,4,9(11),15-tetraene-3,20-dione (VIB, Example 18, 538 mg of the mixed isomers) in toluene (5 ml) and methanol (0.7 ml). The mixture was heated at 85° in a sealed vial until the reaction was complete. The reaction mixture was poured into a buffer solution and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over sodium sulfate, and concentrated to a solid which is recrystallized from ethyl acetate to give the title compound. NMR (CDCl3) 0.70, 1.36, 2.26, 5.10, 5.51, 6.00, 6.20 and 7.17 δ.

후처리

  1. temperatureThe mixture was heated at 85° in a sealed vial until the reaction
  2. additionThe reaction mixture was poured into a buffer solution
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a solid which
  8. customis recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-541f6c4197304912a224ad5390c641f9
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04567001

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