Benzene → 1-tert-Butyl 4-methyl 4-(4-chlorophenyl)piperidine-1,4-dicarboxylate

HRID 556950ノート

反応式

HRID 556950 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[CH3:24][O:15][C:14]([C:11]1([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]1)=[O:16]

参加物

5

反応物 3

HCID 241BenzeneHCID 167693TrimethylsilyldiazomethaneHCID 248288571-(Tert-butoxycarbonyl)-4-(4-chlorophenyl)piperidine-4-carboxylic acid

生成物 1

HCID 497602451-tert-Butyl 4-methyl 4-(4-chlorophenyl)piperidine-1,4-dicarboxylate収率 88%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred 4-(4-chloro-phenyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (852 mg, 2.5 mmol) in methanol (5 ml)-benzene (17.5 ml) was added 15 ml (trimethylsilyl)diazomethane (2.0 M solution in hexanes) at room temperature. The mixture was stirred for 16 hours at room temperature and concentrated in vacuo. The residual yellow oil was purified by silica gel chromatography eluting with hexane-ethyl:acetate (9:1) to give the corresponding ester (780 mg, 88%).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residual yellow oil was purified by silica gel chromatography
  3. washeluting with hexane-ethyl:acetate (9:1)

出典と根拠

ORDレコード
ord-ae8065702e844b7084eedc41639c9680
出典データセット
uspto-grants-2011_11
特許番号
US08058287B2

反応ノート

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