Triacetoxyperiodinane → 2-(4-Fluoro-phenyl)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1644819노트

반응식

HRID 1644819 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH:13]=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 667735772-(4-Fluoro-phenyl)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 866356232-(4-Fluoro-phenyl)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester수율 106.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 2-(4-fluoro-phenyl)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (3.9 g) in a round bottom flask was added Dess-Martin periodinane solution (47 mL of a 15% solution in DCM, CAS [87413-09-0]) and the reaction mixture was stirred for 5 hours at RT. The reaction mixture was then quenched with saturated aqueous sodium thiosulfate solution (25 mL) and stirred a further 20 minutes. The phases were separated and the aqueous was extracted with further DCM (25 mL). The combined organic phases were washed with saturated sodium bicarbonate solution and dried over sodium sulfate. Filtration of the drying agent and evaporation of the volatiles in vacuo afforded the desired 2-(4-fluoro-phenyl)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (4.13 g, MS (ES+): 294.1 (MH+)) as a brown solid which was taken into the next step without further purification.

후처리

  1. customThe reaction mixture was then quenched with saturated aqueous sodium thiosulfate solution (25 mL)
  2. stirringstirred a further 20 minutes
  3. customThe phases were separated
  4. extractionthe aqueous was extracted with further DCM (25 mL)
  5. washThe combined organic phases were washed with saturated sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration of the drying agent and evaporation of the volatiles in vacuo

출처 및 근거

ORD 기록
ord-0743f584853140efbd7affb7db0cec47
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124636B2

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