4-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester → 6-{2-{Ethyl[4-(1-methylpiperidin-4-yl)benzyl]amino}-5-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950210Notes

Reaction equation

HRID 1950210 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([O:22]C(=O)C(C)(C)C)[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2].C(O[C:34]([N:36]1[CH2:41][CH2:40][CH:39]([C:42]2[CH:47]=[CH:46][C:45]([C:48](O)=O)=[CH:44][CH:43]=2)[CH2:38][CH2:37]1)=O)(C)(C)C>>[CH2:1]([N:3]([CH2:48][C:45]1[CH:44]=[CH:43][C:42]([CH:39]2[CH2:40][CH2:41][N:36]([CH3:34])[CH2:37][CH2:38]2)=[CH:47][CH:46]=1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2]

Participants

3

Reactant 2

HCID 224928594-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 57934366Pivalic acid 6-(2-ethylamino-5-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579345216-{2-{Ethyl[4-(1-methylpiperidin-4-yl)benzyl]amino}-5-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 78.7%

Procedure

Synthesized from pivalic acid 6-(2-ethylamino-5-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (50 mg) and 4-(4-carboxyphenyl)piperidine-1-carboxylic acid tert-butyl ester (100 mg) according to an analogous synthetic method to Example 337 described below, the title compound (50 mg) was obtained.

Sources & evidence

ORD record
ord-9769269dccfc41cea629306dd58648f3
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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