Hydrochloric Acid → 1-[4-(Methoxymethyl)phenyl]-1-(4-methoxyphenyl)methanamine

HRID 2059739ノート

反応式

HRID 2059739 の反応式
[CH3:1][O:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([Mg]Br)=[CH:16][CH:15]=1.[BH4-].[Na+].Cl>C1COCC1>[CH3:1][O:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[NH2:9])=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 132851414-(Methoxymethyl)benzonitrileHCID 178491912HCID 178491912、化合物

生成物 1

HCID 578784351-[4-(Methoxymethyl)phenyl]-1-(4-methoxyphenyl)methanamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the product of Step A (1.5 g, 10.19 mmol) in THF (15 mL) was added 4-methoxyphenylmagnesium bromide (11.21 mL, 11.21 mmol, 1.0 M). The reaction aged at rt for 3.5 h and was concentrated. The residue was dissolved in MeOH (20 mL) and then slowly treated with NaBH4 (0.386 g, 10.19 mmol). The reaction was stirred at rt overnight, concentrated and treated with aq. HCl (15 mL, 30 mmol, 2.0 M). The aqueous portion was extracted with EtOAc (2×) and the combined organic layers were washed with a 1:1 solution of aq. 2.0 M NaOH/brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-100% EtOAc/hexane to afford the title compound. HPLC/MS: 241.0 (M—NH2)+; Rt=1.91 min.

後処理

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in MeOH (20 mL)
  3. concentrationconcentrated
  4. extractionThe aqueous portion was extracted with EtOAc (2×)
  5. washthe combined organic layers were washed with a 1:1 solution of aq. 2.0 M NaOH/brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel gradient
  10. washeluted with 0-100% EtOAc/hexane

出典と根拠

ORDレコード
ord-567b65bee85b4e419bb074de8ec161ab
出典データセット
uspto-grants-2012_10
特許番号
US08278304B2

反応ノート

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