4-(3-Fluoro-phenoxymethyl)-pyrroline-1,2-dicarboxylic acid di-tert-butyl ester → (2S,4S)-4-(3-fluoro-phenoxymethyl)-pyrrolidine-2-carboxylic acid

HRID 2113919노트

반응식

HRID 2113919 반응식
C(OC([N:8]1[CH2:12][CH:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:10]=[C:9]1[C:22]([O:24]C(C)(C)C)=[O:23])=O)(C)(C)C>Cl.O1CCOCC1>[F:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][CH2:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10]1

참가 물질

4

반응물 1

HCID 669401524-(3-Fluoro-phenoxymethyl)-pyrroline-1,2-dicarboxylic acid di-tert-butyl ester

생성물 1

HCID 10376960(2S,4S)-4-(3-fluoro-phenoxymethyl)-pyrrolidine-2-carboxylic acid

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

4-(3-fluoro-phenoxymethyl)-pyrroline-1,2-dicarboxylic acid di-tert-butyl ester (Preparation 5, 475 mg, 1.2 mmol) was dissolved in a solution of anhydrous hydrogen chloride in dioxane (4M, 15 ml) and stirred at 50° C. under a nitrogen atmosphere for 1 hour. The solvent was removed under reduced pressure and the resulting semi-solid triturated with ethyl acetate to give a white solid which was recrystallised from ethyl acetate/isopropyl alcohol to give the title compound as a mixture of diastereomers (˜5:1 2S,4S:2S,4R) as a white solid hydrochloride salt (90 mg, 35%)

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting semi-solid triturated with ethyl acetate
  3. customto give a white solid which
  4. customwas recrystallised from ethyl acetate/isopropyl alcohol

출처 및 근거

ORD 기록
ord-2fc530a0aa1f4592b522c7a923c1165c
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432299B2

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