Methyl morpholine oxide → 1-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile

HRID 1672503ノート

反応式

HRID 1672503 の反応式
[OH:1][CH:2]([CH:24]([O:26][CH2:27][O:28][CH3:29])[CH3:25])[CH2:3][N:4]1[C:9]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][C:7]([C:17]([F:20])([F:19])[F:18])=[C:6]([C:21]#[N:22])[C:5]1=[O:23].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:29][O:28][CH2:27][O:26][CH:24]([CH3:25])[C:2](=[O:1])[CH2:3][N:4]1[C:9]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][C:7]([C:17]([F:18])([F:19])[F:20])=[C:6]([C:21]#[N:22])[C:5]1=[O:23]

参加物

5

反応物 2

HCID 82029Methyl morpholine oxideHCID 673389801-(2-Hydroxy-3-methoxymethoxy-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile

生成物 1

HCID 673402801-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile収率 90%

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

1-(2-Hydroxy-3-methoxymethoxy-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile 29 (0.21 g, 0.52 mmoles) was combined with N-methylmorpholine N-oxide (NMO, 92 mg, 0.79 mmoles) and 4 Å molecular sieves (powder, 170 mg) in 5 mL of anhydrous DCM within a 7 mL reaction vial. The mixture was stirred at room temperature for 10 min. After this period tetrapropylammonium perruthenate (TPAP, 10 mg, 0.028 mmoles) was added and the mixture was stirred at room temperature for an additional 3 hours. After this period the reaction mixture was purified directly using flash silica chromatography (0-40% EtOAc/Hexane) to yield 0.191 g (90% yield) of 1-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile as a yellow residue.

後処理

  1. stirringthe mixture was stirred at room temperature for an additional 3 hours
  2. customAfter this period the reaction mixture was purified directly

出典と根拠

ORDレコード
ord-aea83a1d4c4c483da26a634eea95f117
出典データセット
uspto-grants-2011_08
特許番号
US07998986B2

反応ノート

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