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[1,1-Dioxo-(3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluoro-benzyl)-piperidin-1-yl]-methanone → [(3R,4S)-4-Amino-1,1-dioxo-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluorobenzyl)-piperidin-1-yl]-methanone

HRID 497499
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HRID 497499 반응식
[O:1]=[S:2]1(=[O:32])[CH2:6][C@@H:5]([NH:7][C@@H](C2C=CC=CC=2)C)[C@H:4]([C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH2:19]2)=[O:17])[CH2:3]1>[OH-].[Pd+2].[OH-].CO>[NH2:7][C@@H:5]1[CH2:6][S:2](=[O:1])(=[O:32])[CH2:3][C@H:4]1[C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:19]1)=[O:17]
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참가 물질

4

반응물 1

HCID 69747758[1,1-Dioxo-(3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluoro-benzyl)-piperidin-1-yl]-methanone

생성물 1

HCID 69748830[(3R,4S)-4-Amino-1,1-dioxo-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluorobenzyl)-piperidin-1-yl]-methanone수율 108.3%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

[1,1-Dioxo-(3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophen-3-yl]-[(S)-3-(4-fluoro-benzyl)-piperidin-1-yl]-methanone (790 mg, 1.72 mmol), palladium hydroxide (20 weight % on carbon, dry basis; 1.1 g) and methanol (50 mL) were combined in a pressure bottle and shaken under a hydrogen atmosphere (55-60 psig) for 20.5 h. The mixture was filtered through Celite, and the solids were washed thoroughly with methanol. The filtrate was concentrated to give the product as a solid (660 mg, quantitative), used without further purification.

후처리

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were washed thoroughly with methanol
  3. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-032dbf383d9b4fb1a5bbbe6bdf2f1471
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06949546B2

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