Tert-butyl 3-(4-bromobenzoyl)pyrrolidine-1-carboxylate → HCID 68953107、化合物

HRID 2384930ノート

反応式

HRID 2384930 の反応式
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[O:21])=[CH:15][CH:16]=1

参加物

4

反応物 1

HCID 67239763Tert-butyl 3-(4-bromobenzoyl)pyrrolidine-1-carboxylate

生成物 1

HCID 68953107HCID 68953107、化合物収率 82.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

Stir a solution of 3-(4-bromo-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.79 g, 10.7 mmol) in 4 M HCl in dioxane (21.4 mL) at 0° C. for one hour. Concentrate the reaction mixture, dilute the mixture with CH2Cl2, wash with 5 N NaOH (15 mL), and back extract the aqueous with CH2Cl2. Wash the combined organic layer with brine, dry over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph, eluting with 5-10% in MeOH (2N NH3)/CH2Cl2 to give 2.24 g (82%) of the title compound. LC-MS m/z (79Br) 254.0 [M+H]+.

後処理

  1. concentrationConcentrate the reaction mixture
  2. additiondilute the mixture with CH2Cl2
  3. washwash with 5 N NaOH (15 mL)
  4. extractionback extract the aqueous with CH2Cl2
  5. washWash the combined organic layer with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the crude material by flash chromatograph
  10. washeluting with 5-10% in MeOH (2N NH3)/CH2Cl2

出典と根拠

ORDレコード
ord-296658d0ff634a36a141ca9faa3afee6
出典データセット
uspto-grants-2012_09
特許番号
US08263772B2

反応ノート

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