Sodium Hydroxide → (+-)-N-(cyclopropylmethyl)-1,2,3,4-tetrahydro-8-methoxy-2-naphthalenamine hydrochloride

HRID 1078070

反応式

HRID 1078070 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=O)[CH2:10][CH2:9][CH2:8]2.[ClH:14].CN[CH:17]1[CH2:19][CH2:18]1.CC([O-])=O.[Na+].[BH3-][C:26]#[N:27].[Na+].[OH-].[Na+]>CO.C1COCC1.O.CC(O)=O>[ClH:14].[CH:17]1([CH2:26][NH:27][CH:10]2[CH2:9][CH2:8][C:7]3[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=3)[CH2:11]2)[CH2:18][CH2:19]1

参加物

9

反応物 5

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 112753358-Methoxy-3,4-dihydronaphthalen-1(2H)-oneHCID 18546974N-methylcyclopropanamine hydrochloride

生成物 1

HCID 18331788(+-)-N-(cyclopropylmethyl)-1,2,3,4-tetrahydro-8-methoxy-2-naphthalenamine hydrochloride

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a solution of 2.64 g (15 mmol) 8-methoxy tetralone, 6 g (60 mmol) methylcyclopropylamine HCl and 4.92 g (60 mmol) NaOAc in 30 mL MeOH/THF (1:1) was added HOAc dropwise to adjust the pH to 4-5. The reaction mixture stirred for 15 minutes under N2, then 1.26 g (20 mmol) NaCNBH3 was added. When the reaction was complete by TLC (24 h), 1N NaOH (20 mL) and H2O (200mL) was added to quench the reaction. The solution was extracted with CH2Cl2 (2×500 mL) and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting oil was purified by liquid chromatography on 400 g of silica gel 60 (230-400m), eluting with hexane/acetone (3:1). Fractions homogeneous by TLC were combined and concentrated in vacuo to give pure compound as an oil. The HCl salt was formed by using a MeOH/HCl solution. The title compound was recovered by recrystallization as a white solid using EtOAc/MeOH (1.77 g, 44%); m.p. 216°-218° C.

後処理

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionThe solution was extracted with CH2Cl2 (2×500 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting oil was purified by liquid chromatography on 400 g of silica gel 60 (230-400m)
  10. washeluting with hexane/acetone (3:1)
  11. concentrationconcentrated in vacuo
  12. customto give pure compound as an oil

出典と根拠

ORDレコード
ord-0befaaf73ea74a969b2dcb92bf7f6f38
出典データセット
uspto-grants-1996_08
特許番号
US05545755

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