Tert-butyl 3-(4-bromobenzoyl)pyrrolidine-1-carboxylate → HCID 68953107, 화합물

HRID 2384930노트

반응식

HRID 2384930 반응식
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

참가 물질

4

반응물 1

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

생성물 1

HCID 68953107HCID 68953107, 화합물수율 82.4%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-296658d0ff634a36a141ca9faa3afee6
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263772B2

반응 노트

불러오는 중…