Phthalimide → (2R)-tert-butyl 2-(2-(3-chloro-4-fluorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)pyrrolidine-1-carboxylate

HRID 2279589노트

반응식

HRID 2279589 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9](O)[CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[CH:6][C:7]=1[F:8].[C:24]1(=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[NH:25]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:25]2[C:26](=[O:33])[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24]2=[O:34])[CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86705571(2R)-tert-butyl 2-(2-(3-chloro-4-fluorophenyl)-2-hydroxyethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 86705572(2R)-tert-butyl 2-(2-(3-chloro-4-fluorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)pyrrolidine-1-carboxylate수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 301 (0.0754 g, 0.219 mmol), isoindoline-1,3-dione (0.0387 g, 0.263 mmol) and PPh3 (0.127 g, 0.482 mmol) in THF cooled to 0° C. was added DEAD (0.0760 mL, 0.482 mmol) and the reaction warmed to RT and stirred overnight. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2SO4) filtered and concentrated to an oil. The crude oil was purified by SiO2 chromatography to afford 0.0507 g (49%) of (2R)-tert-butyl 2-(2-(3-chloro-4-fluorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)pyrrolidine-1-carboxylate (303) as a clear oil.

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe crude oil was purified by SiO2 chromatography

출처 및 근거

ORD 기록
ord-72246da9a3f543bb8045bf7f7585e988
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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