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

HRID 43353노트

반응식

HRID 43353 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-758b8aff5c324789a35f03191e911f1b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536182B2

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