4-Bromobenzaldehyde → 1,1-Dimethylethyl (2R,6S)-4-[(4-bromophenyl)methyl]-2,6-dimethyl-1-piperazinecarboxylate

HRID 43353

反応式

HRID 43353 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C@@H:11]1[CH2:16][NH:15][CH2:14][C@H:13]([CH3:17])[N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:15]2[CH2:16][C@H:11]([CH3:10])[N:12]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[C@H:13]([CH3:17])[CH2:14]2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 707414-BromobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21021901tert-Butyl (2R,6S)-2,6-dimethylpiperazine-1-carboxylate

生成物 1

HCID 252240971,1-Dimethylethyl (2R,6S)-4-[(4-bromophenyl)methyl]-2,6-dimethyl-1-piperazinecarboxylate収率 91.8%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A mixture of 4-bromobenzaldehyde (1.85 g, 10 mmol), 1,1-dimethylethyl (2R,6S)-2,6-dimethyl-1-piperazinecarboxylate (2.15 g, 10 mmol) and sodium triacetoxyborohydride (3.18 g) in 1,2-DCE (35 ml) was stirred at room temperature for 3 days. Saturated aq. NaHCO3 solution was added and the mixture stirred for 30 mins. The product was extracted into EtOAc and the extracts dried (Na2SO4) and concentrated. The residue was dissolved in DCM and treated with PS-hydrazine resin with stirring for 2 h. The resin was removed by filtration and the solvent removed in vacuo. Chromatography (0-40% EtOAc/hexane) gave the title compound (3.52 g). MS (ES): MH+ 383/385.

後処理

  1. stirringthe mixture stirred for 30 mins
  2. extractionThe product was extracted into EtOAc
  3. dry with materialthe extracts dried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in DCM
  6. additiontreated with PS-hydrazine resin
  7. stirringwith stirring for 2 h
  8. customThe resin was removed by filtration
  9. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-758b8aff5c324789a35f03191e911f1b
出典データセット
uspto-grants-2013_09
特許番号
US08536182B2

関連ノート

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