2,5-Dibromopyridine → 3-(5-Bromo-pyridine-2-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 423393

반응식

HRID 423393 반응식
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][N:8]=1.[C:14]([O:18][C:19]([N:21]1[CH2:25][CH2:24][CH:23]([C:26](=[O:31])N(OC)C)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[C:14]([O:18][C:19]([N:21]1[CH2:25][CH2:24][CH:23]([C:26]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][N:8]=2)=[O:31])[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 693532,5-DibromopyridineHCID 57419605Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylateHCID 178418339Butyllithium

생성물 1

HCID 666738453-(5-Bromo-pyridine-2-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester수율 43%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
-80 °C

실험 절차

Add dropwise n-BuLi (3.2 mL, 5.1 mmol) to an suspension of 2,5-dibromopyridine (1.0 g, 4.2 mmol) in dry toluene (50 mL) at −80° C. under nitrogen. Allow the mixture to stir at −80° C. for 2 h. Slowly add a solution of 3-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.4 g, 5.5 mmol) in dry toluene (10 mL). Allow the reaction mixture to stir for 1 h at −78° C., then warm to −10° C. Quench the mixture with saturated NH4Cl (1 mL) and warm to RT. Separate the organic layer and concentrate. Purify the crude material by flash chromatography, eluting with 10-20% ethylacetate/hexane to give 0.61 g (43%) of the title compound. LC-MS/ES m/z (79Br) 299 [M-tert-Bu+H]+.

후처리

  1. stirringto stir for 1 h at −78° C.
  2. temperaturewarm to −10° C
  3. customQuench the mixture with saturated NH4Cl (1 mL)
  4. temperaturewarm to RT
  5. customSeparate the organic layer
  6. concentrationconcentrate
  7. customPurify the crude material by flash chromatography
  8. washeluting with 10-20% ethylacetate/hexane

출처 및 근거

ORD 기록
ord-43c18ff452f74b25851cdba05be5e396
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101764B2

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