Diazomethane diethylether → tert-butyl (1R*,4S*,6R*)-4-({[(4-nitrophenyl)carbonyl]oxy}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate

HRID 1052231ノート

反応式

HRID 1052231 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12][CH2:13][CH:14]2[CH2:19][CH:18]=[CH:17][CH2:16][N:15]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+](=[CH2:29])=[N-].C(OCC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH2:13][C@@H:14]2[CH2:19][C@@H:18]3[C@@H:17]([CH2:29]3)[CH2:16][N:15]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

4

反応物 2

HCID 21186548Diazomethane diethyletherHCID 71147221tert-butyl 2-({[(4-nitrophenyl)carbonyl]oxy}methyl)-3,6-dihydropyridine-1(2H)-carboxylate

生成物 1

HCID 86676232tert-butyl (1R*,4S*,6R*)-4-({[(4-nitrophenyl)carbonyl]oxy}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

実験手順

tert-Butyl 2-{[(4-nitrophenyl)carbonyl]oxy}methyl)-3,6-dihydropyridine-1(2H)-carboxylate (10.0 g) produced above was dissolved in 5% diazomethane/diethyl ether (1.4 L), palladium acetate (689 mg) was added at 10° C., and the mixture was stirred at the same temperature for 40 min. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give a mixture of tert-butyl 2-({[(4-nitrophenyl)carbonyl]oxy}methyl)-3,6-dihydropyridine-1(2H)-carboxylate and the title compound. The obtained mixture was subjected to 3 repeats of a similar reaction operation to give the title compound (8.4 g).

後処理

  1. customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/petroleum ether)
  2. customto give

出典と根拠

ORDレコード
ord-771d009b8cb347bdab1fd4fb38327510
出典データセット
uspto-grants-2016_07
特許番号
US09388195B2

反応ノート

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