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

HRID 1433997Notes

Reaction equation

HRID 1433997 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-076f0086fbcd4a7e8648c44c418d4911
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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