Acetaldehyde → HCID 69179394、化合物

HRID 409677

反応式

HRID 409677 の反応式
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:2].[Na+].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1)([O-:17])=[O:16].C(=O)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:27]1[CH2:26][CH2:25][CH:24]([C:21]2[CH:22]=[CH:23][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[CH2:29][CH2:28]1)[CH3:2]

参加物

6

反応物 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 159258174-(4-Nitrophenyl)piperidine

生成物 1

HCID 69179394HCID 69179394、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
5 °C

実験手順

Sodium triacetoxyborohydride (3.1 g, 14.6 mmol, 3 equiv) is added to a cold (5° C.) solution of 4-(4-nitro-phenyl)-piperidine (1 g, 4.9 mmol) and acetaldehyde (0.82 mL, 14.6 mmol, 3 equiv) in DCM (20 mL). The reaction mixture is stirred for 1 h at 5° C. and then diluted with DCM and a saturated aqueous solution of NaHCO3. The layers are separated and the aqueous layer is extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 98:2) to provide the title compound as a yellow oil. ESI-MS: 235.1 [MH]+; tR=2.64 min (purity: 85%, system 1); TLC: Rf=0.14 (DCM/MeOH+1% NH3aq, 98:2).

後処理

  1. customThe layers are separated
  2. extractionthe aqueous layer is extracted with DCM
  3. washThe organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 98:2)

出典と根拠

ORDレコード
ord-994abab701f7404d89fd24d4e092ec07
出典データセット
uspto-grants-2014_06
特許番号
US08759517B2

関連ノート

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