Sodium Sulfate → 2-Amino-1-(3,4-dimethoxyphenyl)-5,5-ethylenedioxy-7-(4-methoxyphenyl)heptane

HRID 256195Notes

Reaction equation

HRID 256195 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][CH:18]([N+:36]([O-])=O)[CH2:19][CH2:20][C:21]2([O:35][CH2:34][CH2:33][O:32]2)[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH2:36][CH:18]([CH2:19][CH2:20][C:21]1([O:32][CH2:33][CH2:34][O:35]1)[CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[CH2:17][C:11]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([O:8][CH3:7])[CH:10]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 130650211-(3,4-Dimethoxyphenyl)-5,5-ethylenedioxy-7-(4-methoxyphenyl)-2-nitroheptaneHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 135888472-Amino-1-(3,4-dimethoxyphenyl)-5,5-ethylenedioxy-7-(4-methoxyphenyl)heptane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 6.6 g. (0.174 mole) of LiAlH4 in 200 ml. of dry tetrahydrofuran was added dropwise a solution of 25 g. (0.058 mole) of 1-(3,4-dimethoxyphenyl)-5,5-ethylenedioxy-7-(4-methoxyphenyl)-2-nitroheptane in 100 ml. of dry THF at room temperature at such a rate as to control reflux of reaction solution. After addition of substrate was completed, the reaction mixture was refluxed under N2 for 2 hours, and cooled to ice bath temperature. The excess LiAlH4 was decomposed with saturated Na2SO4 solution. The inorganic salt was filtered off and thoroughly washed with ethyl acetate and chloroform. The filtrate was concentrated in vacuo to give 28 g. of brown, oily product. Without further purification, the amino ketal derivative was used for the next reaction.

Workup

  1. additionTo a suspension of 6.6 g
  2. additionAfter addition of substrate
  3. temperaturethe reaction mixture was refluxed under N2 for 2 hours
  4. temperaturecooled to ice bath temperature
  5. filtrationThe inorganic salt was filtered off
  6. washthoroughly washed with ethyl acetate and chloroform
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give 28 g
  9. customWithout further purification
  10. customthe amino ketal derivative was used for the next reaction

Sources & evidence

ORD record
ord-44656b1dc507413c8b1c4534d22aedea
Source dataset
uspto-grants-1987_10
Patent number
US04701461

Reaction notes

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