3,5-Dichlorophenol → n-Tert-butoxycarbonyl-4-(3,5-dichlorophenoxy)piperidine

HRID 2185479노트

반응식

HRID 2185479 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[Cl:34][C:35]1[CH:36]=[C:37](O)[CH:38]=[C:39]([Cl:41])[CH:40]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:33][C:37]2[CH:36]=[C:35]([Cl:34])[CH:40]=[C:39]([Cl:41])[CH:38]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

참가 물질

6

반응물 4

HCID 115713,5-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

생성물 1

HCID 22458487n-Tert-butoxycarbonyl-4-(3,5-dichlorophenoxy)piperidine수율 78.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triphenylphosphine (786 mg) was added to a solution of N-tert-butoxycarbonyl-4-hydroxypiperidine (603 mg), 3,5-dichlorophenol (489 mg) and diethyl azodicarboxylate (522 mg) in tetrahydrofuran (15 mL) at room temperature. After stirring at room temperature for 14 hr, the reaction mixture was evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6) to give the titled compound (815 mg) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 9H), 1.75 (m, 2H), 1.90 (m, 2H), 3.37 (m, 2H), 3.66 (m, 2H), 4.44 (m, 1H), 6.80 (d, J=1.5 Hz, 2H), and 6.95 (s, 1H); mass spectrum (EI+) m/e 345 (M).

후처리

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6)

출처 및 근거

ORD 기록
ord-64ab112964fc4ee797f7219fe2037cf1
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06399629B1

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