m-(Trifluoromethyl)nitrobenzene → Tert-butyl 4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

HRID 1796206

반응식

HRID 1796206 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]([F:28])([F:27])[C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1O.FC(F)(F)C1C=C([N+]([O-])=O)C=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.N(C(OCC)=O)=NC(OCC)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:18]2[CH:19]=[CH:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][C:17]=2[C:16]([F:15])([F:27])[F:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 7386m-(Trifluoromethyl)nitrobenzeneHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 3014014Phenol, 4-nitro-2-(trifluoromethyl)-

생성물 1

HCID 22181018Tert-butyl 4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate수율 88%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 220568ethyl N-ethoxycarbonyliminocarbamate용매

실험 절차

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (1.45 g), 2-trifluoromethyl-4-nitrophenol (1.38 g), which was prepared from 3-trifluoromethylnitrobenzene according to the method described in J. Org. Chem., 63, 4199 (1998), and triphenylphosphine (2.27 g) in dichloromethane (65 ml), diethyl azodicarboxylate (1.4 ml) was added dropwise with stirring under ice-cooling, and the resulting mixture was stirred at room temperature overnight and then evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using dichloromethane as the eluent to afford the title compound (2.28 g, yield: 88%) as a pale yellow oil.

후처리

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customevaporated in vacuo
  4. customThe residue obtained
  5. customwas purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-2c2b93391aae4db1b0cec91fb04f56ba
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030138B2

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