Acetic Acid → (R)-methyl 4-(1-((1-methylcyclohexyl)methylamino)ethyl)benzoate

HRID 1049100ノート

反応式

HRID 1049100 の反応式
[NH2:1][C@@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3].CO.[CH3:16][C:17]1([CH:23]=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(O)(=O)C.C([BH3-])#N.[Na+]>>[CH3:16][C:17]1([CH2:23][NH:1][C@@H:2]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[CH3:3])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

参加物

6

反応物 5

HCID 176Acetic AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 111371681-Methylcyclohexane-1-carboxaldehydeHCID 17751897(R)-Methyl 4-(1-aminoethyl)benzoate

生成物 1

HCID 67395199(R)-methyl 4-(1-((1-methylcyclohexyl)methylamino)ethyl)benzoate収率 63.4%

実験手順

To a solution of (R)-methyl 4-(1-aminoethyl)benzoate (0.12 g, 0.67 mmol) in methanol (2.97 mL, 73.33 mmol) was added 1-methylcyclohexane-1-carboxaldehyde (0.093 g, 0.74 mmol) and acetic acid (0.152 mL, 2.67 mmol). The reaction was stirred for 1 hour at room temperature whereupon sodium cyanoborohydride (63.1 mg, 1.00 mmol) was added and the mixture further stirred at room temperature overnight. The solvent was evaporated and the residual sodium cyanoborohydride quenched with saturated aqueous NaHCO3. The mixture was extracted into ethyl acetate, the organic layer washed with brine and the solvent evaporated to dryness. The residue obtained was purified via silica chromatography (0-5% MeOH/DCM) to afford the title compound as a colorless oil (123.0 mg, 63%). LC-MS: (FA) ES+ 290.

後処理

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe residual sodium cyanoborohydride quenched with saturated aqueous NaHCO3
  4. extractionThe mixture was extracted into ethyl acetate
  5. washthe organic layer washed with brine
  6. customthe solvent evaporated to dryness
  7. customThe residue obtained
  8. customwas purified via silica chromatography (0-5% MeOH/DCM)

出典と根拠

ORDレコード
ord-ef45cbb639e541f79c24a6a042314063
出典データセット
uspto-grants-2016_07
特許番号
US09382197B2

反応ノート

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