Hydrochloric Acid → HCID 178515504, 화합물

HRID 2235278노트

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HRID 2235278 반응식
C([Si](C)(C)[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:9][CH2:8]1)(C)(C)C.[Li+].CC([N-]C(C)C)C.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Br)=[C:32]([Cl:38])[CH:31]=1.Cl>CO.O.C1COCC1>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH:15]2[CH2:16][CH2:17][N:13]([C@H:10]3[CH2:9][CH2:8][C@@H:7]([OH:6])[CH2:12][CH2:11]3)[C:14]2=[O:18])=[C:32]([Cl:38])[CH:31]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 2724682Lithium diisopropylamideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneHCID 178455336HCID 178455336, 화합물

생성물 1

HCID 178515504HCID 178515504, 화합물수율 70%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Charge a flask with cis-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (Preparation 17) (1.0 g, 3.4 mmol), dissolve with THF (0.2 M) and cool to −78° C. Add LDA (1.1 to 1.5 eq) and stir at −78° C. for 5 minutes. Add 4-bromo-1-bromomethyl-2-chloro-benzene (1.4 g, 5.0 mmol) and warm to room temperature overnight. Dilute with methanol (0.2 M) and add concentrated HCl (10 eq.) and stir at room temperature. Pour into water after reaction complete by HPLC and extract with methylene chloride, dry over sodium sulfate, filter and concentrate in vacuo. Purify the residue over silica gel (20% hexane in ethyl acetate) to afford 911 mg (70%) of the title compound: Mass spectrum (apci) m/z=387.9 (M+H).

후처리

  1. customafter reaction complete by HPLC
  2. extractionextract with methylene chloride
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue over silica gel (20% hexane in ethyl acetate)

출처 및 근거

ORD 기록
ord-3ee8ccc895934d36a77fb0df5c67f78b
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713979B2

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