Nitroethane → tert-Butyl 6-cyano-2-pyridylmethylcarbamate

HRID 499352ノート

反応式

HRID 499352 の反応式
C[N+:2]([O-])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12]N=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C[Si](C#[N:22])(C)C.CN(C)C(Cl)=O.[N+:29]([CH2:32][CH3:33])([O-])=O>>[C:32]([C:33]1[N:22]=[C:15]([CH2:10][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH:14]=[CH:13][CH:12]=1)#[N:29]

参加物

5

反応物 4

HCID 6587NitroethaneHCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86596460tert-butyl methyl(2-pyridyl)carbamate N-oxide

生成物 1

HCID 22939432tert-Butyl 6-cyano-2-pyridylmethylcarbamate収率 77%

実験手順

A mixture of tert-butyl methyl(2-pyridyl)carbamate N-oxide (14.1 g, 63 mmol), trimethylsilyl cyanide (12.5 g, 126 mmol), N,N-dimethylcarbamoyl chloride (13.5 g, 125 mmol) and nitroethane (120 ml) was stirred at room temperature for 48 hrs. The reaction mixture was concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (10:1, v/v) and recrystallized from ethyl acetate-hexane to give the titled compound (11.3 g, 77%).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washeluted with hexane-ethyl acetate (10:1
  3. customv/v) and recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-9d10c311de32489ca938bb3545092a02
出典データセット
uspto-grants-2010_08
特許番号
US07767665B2

反応ノート

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