Triphenylphosphine → 4-[3-(3-Nitro-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1843605ノート

反応式

HRID 1843605 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][CH:50](O)[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:42])[CH3:41].CCOC(/N=N/C(OCC)=O)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][CH:50]([N:12]2[CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:11]2)[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:41])[CH3:42]

参加物

7

反応物 5

HCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 178526612HCID 178526612、化合物

生成物 1

HCID 671840714-[3-(3-Nitro-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 4-[3-(3-nitro-phenyl)-1H-pyrazol-4-yl]-pyridine (200 mg, 0.750 mmol) in anhydrous tetrahydrofuran (3 mL) at 0° C. triphenylphosphine (293 mg, 1.12 mmol, 1.5 eq), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 0.750 mmol, 1 eq) and DEAD (176 μL, 1.12 mmol, 1.5 eq) were added. The reaction was allowed to warm to room temperature and stirred under nitrogen atmosphere overnight. The regioisomeric ratio was 1:4 at 254 nm in favor of the N1-alkylated product. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (DCM/ethanol 97:3) to give 950 mg of major regioisomer contaminated with triphenylphosphinoxide.

後処理

  1. additionwere added
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (DCM/ethanol 97:3)
  4. customto give 950 mg of major regioisomer

出典と根拠

ORDレコード
ord-6f1ca0bdcdcf4fc3a65086352d29c924
出典データセット
uspto-grants-2015_02
特許番号
US08946250B2

反応ノート

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