Chlorosuccinimide → 1-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole

HRID 1634715ノート

反応式

HRID 1634715 の反応式
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[Cl:19]N1C(=O)CCC1=O>CN(C=O)C>[Cl:19][C:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[C:6]([O:5][CH2:4][C@@H:2]2[CH2:3][O:1]2)=[CH:7][CH:8]=1.[Cl:19][C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:6]=1[O:5][CH2:4][C@@H:2]1[CH2:3][O:1]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

参加物

5

反応物 2

HCID 31398ChlorosuccinimideHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

生成物 2

HCID 590329461-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazoleHCID 590329593-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-[(2S)-oxiranylmethoxy]-9H-carbazole (0.50 g, 2.09 mmol) and N-chlorosuccinimide (0.280 g, 2.09 mmol) in 5 mL dry DMF was stirred at ambient temperature for 48 hours. The reaction mixture was partitioned with EtOAc and H2O. The organic phase was washed with H2O and dried with Na2SO4. The solvent was removed (rotovap) and the residue purified by flash chromatography (methylene chloride-hexane-1:1) afforded 0.10 g of the title compound plus 0.50 g of 3-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole.

後処理

  1. customThe reaction mixture was partitioned with EtOAc and H2O
  2. washThe organic phase was washed with H2O
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed (rotovap)
  5. customthe residue purified by flash chromatography (methylene chloride-hexane-1:1)

出典と根拠

ORDレコード
ord-420bbba7dd7e4683b5048af95a46fd4b
出典データセット
uspto-grants-2003_01
特許番号
US06506901B2

反応ノート

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