Phthalimide → (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethyl)piperidine-1-carboxylate

HRID 451716노트

반응식

HRID 451716 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)([O:10][CH2:11][CH2:12]O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:15]2)([O:10][CH2:11][CH2:12][N:31]2[C:27](=[O:37])[C:28]3[C:29](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:30]2=[O:32])[CH3:9])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59201466(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)ethyl)piperidine-1-carboxylate

생성물 1

HCID 59201660(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethyl)piperidine-1-carboxylate수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)ethyl)piperidine-1-carboxylate (1.000 g, 2.6 mmol), phthalimide (1.490 g, 10.1 mmol), triphenylphosphine (4.130 g, 15.7 mmol), and DIAD (3.430 g, 17.0 mmol) in THF was stirred at rt for 40 h. After the reaction mixture was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to afford 0.6792 g (51%) of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethyl)piperidine-1-carboxylate. MS ESI +ve m/z 537 (M+Na).

후처리

  1. customAfter the reaction mixture was evaporated under reduced pressure
  2. customthe crude product was purified by reversed-phase HPLC

출처 및 근거

ORD 기록
ord-9555b888116442d585495bf6952c7c3a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

반응 노트

불러오는 중…