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

HRID 1268183

反応式

HRID 1268183 の反応式
[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.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[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]

参加物

7

反応物 5

HCID 7386m-(Trifluoromethyl)nitrobenzeneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 3014014Phenol, 4-nitro-2-(trifluoromethyl)-

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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) was added dropwise diethyl azodicarboxylate (1.4 ml) in an ice bath and the mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane as an eluant to give the desired compound (2.28 g, yield 88%) as a pale yellow oil.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-8892bdb92f49468385d425e8c12bf7a6
出典データセット
uspto-grants-2003_04
特許番号
US06555556B1

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