Ammonia → 6-{2-{[4-(2-Dimethylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950184Notes

Reaction equation

HRID 1950184 reaction equation
C(NC1C=C(OC)C=CC=1C1CCC2C=C(OC(=O)C(C)(C)C)C=CC=2C1)C.CN(C)C(C)(C)COC1C=CC(C=O)=CC=1.[CH3:45][N:46]([CH3:87])[C:47]([CH3:86])([CH3:85])[CH2:48][O:49][C:50]1[CH:84]=[CH:83][C:53]([CH2:54][CH2:55][CH2:56][NH:57][C:58]2[CH:63]=[C:62]([O:64][CH3:65])[CH:61]=[CH:60][C:59]=2[CH:66]2[CH2:75][CH2:74][C:73]3[CH:72]=[C:71]([O:76]C(=O)C(C)(C)C)[CH:70]=[CH:69][C:68]=3[CH2:67]2)=[CH:52][CH:51]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].N>O1CCCC1>[CH3:87][N:46]([CH3:45])[C:47]([CH3:85])([CH3:86])[CH2:48][O:49][C:50]1[CH:51]=[CH:52][C:53]([CH2:54][CH2:55][CH2:56][NH:57][C:58]2[CH:63]=[C:62]([O:64][CH3:65])[CH:61]=[CH:60][C:59]=2[CH:66]2[CH2:75][CH2:74][C:73]3[CH:72]=[C:71]([OH:76])[CH:70]=[CH:69][C:68]=3[CH2:67]2)=[CH:83][CH:84]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 21226445Aluminium lithium hydrideHCID 230872454-(2-Dimethylamino-2-methylpropoxy)benzaldehydeHCID 579340956-(2-(Ethylamino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl pivalateHCID 66626509Pivalic acid 6-{2-{[4-(2-dimethylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 666276626-{2-{[4-(2-Dimethylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Synthesized from pivalic acid 6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester and 4-(2-dimethylamino-2-methylpropoxy)benzaldehyde according to an analogous synthetic method to Example 212, to a solution of the resulting pivalic acid 6-{2-{[4-(2-dimethylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (73 mg) in tetrahydrofuran (1.5 ml) was added lithium aluminum hydride (20 mg), and the solution was stirred for 1.5 hours at room temperature. Tetrahydrofuran and aqueous ammonia were sequentially added thereto followed by stirring. The solution was then filtered through celite pad, the resulting residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system) to provide the title compound (45 mg).

Workup

  1. stirringby stirring
  2. filtrationThe solution was then filtered through celite pad
  3. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-68f498d1844f49cf8c7b98472ce55053
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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