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Lithium diisopropylamide → HCID 178515502, 화합물

HRID 1672739
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HRID 1672739 반응식
[F:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH2:4][CH2:3]1.[Li+].CC([N-]C(C)C)C.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Br)=[C:25]([Cl:31])[CH:24]=1>C1COCC1>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:10]2[CH2:11][CH2:12][N:8]([C@H:5]3[CH2:6][CH2:7][C@@H:2]([F:1])[CH2:3][CH2:4]3)[C:9]2=[O:13])=[C:25]([Cl:31])[CH:24]=1
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참가 물질

5

반응물 3

HCID 2724682Lithium diisopropylamideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneHCID 178516221HCID 178516221, 화합물

생성물 1

HCID 178515502HCID 178515502, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of cis-1-(4-fluoro-cyclohexyl)-pyrrolidin-2-one (Preparation 26) (190 mg, 1.03 mmol) in 5 mL dry THF, add 1.29 mL of 2M LDA (2.5 eq.) in THF dropwise at −78° C. Then, add 16 mg of 4-Bromo-1-bromomethyl-2-chloro-benzene (2 eq) at −78° C. Allow the resulting solution to stand at room temp for overnight. Quench the mixture with saturated aqueous NH4Cl and extract with CH2Cl2. Wash the organic layer with water, brine, dry over Na2SO4, filter and concentrate. Purify the crude material by chromatography to afford the title compound: mass spectrum (m/z): 389 (M+1).

후처리

  1. customQuench the mixture with saturated aqueous NH4Cl
  2. extractionextract with CH2Cl2
  3. washWash the organic layer with water, brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by chromatography

출처 및 근거

ORD 기록
ord-cb5c3a543dd24ceba7aeb9e3e54c65f9
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07998999B2

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