Acetic Acid → 2-(Cyclohexylmethyl)-4,4-dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 2370637ノート

反応式

HRID 2370637 の反応式
[B-]C#N.[Na+].[CH3:5][C:6]1([CH3:19])[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=2)[CH2:9][NH:8][CH2:7]1.C(O)(=O)C.[CH:24]1([CH:30]=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>CO>[CH:24]1([CH2:30][N:8]2[CH2:7][C:6]([CH3:19])([CH3:5])[C:15]3[C:10](=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=3)[CH2:9]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 16275CyclohexanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 20587905Sodium cyanoborohydride [MI]HCID 219596554,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 681944452-(Cyclohexylmethyl)-4,4-dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
35 °C

実験手順

Sodium cyanotrihydroborate (0.600 g, 9.55 mmol) was added to a solution of 4,4-dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (0.600 g, 2.91 mmol), acetic acid (0.210 mL, 3.66 mmol) and cyclohexanecarbaldehyde (0.4 g, 3.57 mmol) in methanol (40 mL). The reaction mixture was stirred at 35° C. for 16 hours. The reaction was neutralized with saturated sodium bicarbonate solution, and the mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified with silica gel column chromatography (3% ethyl acetate/petroleum ether) to provide the title compound.

後処理

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified with silica gel column chromatography (3% ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-ee28d1c4a9b747f7a57b1316f97ad7f7
出典データセット
uspto-grants-2014_04
特許番号
US08710065B2

反応ノート

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