Hydrochloric Acid → HCID 178515504、化合物

HRID 2235278ノート

反応式

HRID 2235278 の反応式
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

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 2724682Lithium diisopropylamideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneHCID 178455336HCID 178455336、化合物

生成物 1

HCID 178515504HCID 178515504、化合物収率 70%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3ee8ccc895934d36a77fb0df5c67f78b
出典データセット
uspto-grants-2010_05
特許番号
US07713979B2

反応ノート

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