Hydrochloric Acid → HCID 178515811、化合物

HRID 1173830ノート

反応式

HRID 1173830 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[CH2:30][C:31]1[S:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[C:32]=1[Cl:40].Cl>CO.O.C1COCC1>[Cl:40][C:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[S:35][C:31]=1[CH2:30][CH:15]1[CH2:16][CH2:17][N:13]([C@H:10]2[CH2:9][CH2:8][C@@H:7]([OH:6])[CH2:12][CH2:11]2)[C:14]1=[O:18]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8167082-(Bromomethyl)-3-chloro-1-benzothiopheneHCID 2724682Lithium diisopropylamideHCID 178455336HCID 178455336、化合物

生成物 1

HCID 178515811HCID 178515811、化合物収率 71%

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 (0.50 g, 1.68 mmol) (1.0 eq), 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 2-bromomethyl-3-chloro-benzo[b]thiophene (U.S. Pat. No. 4,939,140) (0.53 g, 2.02 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. Purification of the residue over silica gel (20% hexane in ethyl acetate) affords the title compound as a white powder (0.44 g, 71%): MS (APCI-pos mode) m/z (rel intensity) 364.1 (100), 366.1 (40).

後処理

  1. temperature4,939,140) (0.53 g, 2.02 mmol) and warm to room temperature overnight
  2. customafter reaction complete by HPLC
  3. extractionextract with methylene chloride
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurification of the residue over silica gel (20% hexane in ethyl acetate)

出典と根拠

ORDレコード
ord-2becacd583fc4e6b955360d28d37b702
出典データセット
uspto-grants-2010_11
特許番号
US07834194B2

反応ノート

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