Triphenylphosphine → Tert-butyl 4-[(6-chloropyridin-2-yl)oxy]piperidine-1-carboxylate

HRID 2074228

반응식

HRID 2074228 반응식
N(C(OCC)=O)=NC(OCC)=O.[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:46][C:47]1[N:52]=[C:51](O)[CH:50]=[CH:49][CH:48]=1>O.C1COCC1>[Cl:46][C:47]1[N:52]=[C:51]([O:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)[CH:50]=[CH:49][CH:48]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 1785160256-chloropyridin-2-ol

생성물 1

HCID 21906058Tert-butyl 4-[(6-chloropyridin-2-yl)oxy]piperidine-1-carboxylate수율 78.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Diethyl azodicarboxylate (11 ml, 40% Tol solution) was dropwise added to a THF (30 ml) solution containing tert-butyl 4-hydroxypiperidine-1-carboxylate (4.6 g), triphenylphosphine (6.1 g) and 6-chloro-2-pyridinol (2.0 g) at 0° C., followed by stirring at room temperature for 24 hours. Water was added to the reaction solution, followed by extraction with EtOAc. The organic layer was washed with an aqueous 1 M sodium hydroxide solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=10:1 (v/v)) to obtain tert-butyl 4-[(6-chloro-2-pyridinyl)oxy]-1-piperidinecarboxylate (3.8 g).

후처리

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with an aqueous 1 M sodium hydroxide solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=10:1 (v/v))

출처 및 근거

ORD 기록
ord-4809178c2d1849d2b66fd43d13dc32be
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919494B2

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