pivalic acid (R)-6-(2-ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester → (R)-6-{2-{[4-(2-Amino-2-methylpropoxy)benzyl]ethylamino}phenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 2423817Notes

Reaction equation

HRID 2423817 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([O:20]C(=O)C(C)(C)C)[CH:14]=[CH:13][C:12]=2[CH2:11]1)[CH3:2].[CH:27]([C:29]1[CH:47]=[CH:46][C:32]([O:33][CH2:34][C:35]([NH:38]C(=O)OC(C)(C)C)([CH3:37])[CH3:36])=[CH:31][CH:30]=1)=O>>[NH2:38][C:35]([CH3:36])([CH3:37])[CH2:34][O:33][C:32]1[CH:31]=[CH:30][C:29]([CH2:27][CH2:2][CH2:1][NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C@@H:10]2[CH2:19][CH2:18][C:17]3[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=3[CH2:11]2)=[CH:47][CH:46]=1

Participants

3

Reactant 2

HCID 57933894pivalic acid (R)-6-(2-ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 57934200Tert-butyl[2-(4-formylphenoxy)-1,1-dimethylethyl]carbamate

Product 1

HCID 66626271(R)-6-{2-{[4-(2-Amino-2-methylpropoxy)benzyl]ethylamino}phenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 29%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) and tert-butyl [2-(4-formylphenoxy)-1,1-dimethylethyl]carbamate (125 mg) according to an analogous synthetic method to Example 238 and purified by LC-MS, the title compound (11 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-10d205fa485f4508af27af115419f2af
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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