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

HRID 1672503노트

반응식

HRID 1672503 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-aea83a1d4c4c483da26a634eea95f117
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998986B2

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