Tert-butyl[2-(4-formylphenoxy)-1,1-dimethylethyl]carbamate → (R)-6-{2-{[4-(2-Amino-2-methylpropoxy)benzyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950231Notes

Reaction equation

HRID 1950231 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C@@H:14]1[CH2:23][CH2:22][C:21]2[CH:20]=[C:19]([O:24]C(=O)C(C)(C)C)[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:2].C(OC(=O)[NH:37][C:38]([CH3:50])([CH3:49])[CH2:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([CH:47]=O)=[CH:43][CH:42]=1)(C)(C)C>>[NH2:37][C:38]([CH3:50])([CH3:49])[CH2:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:2][CH2:1][NH:3][C:4]2[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=2[C@@H:14]2[CH2:23][CH2:22][C:21]3[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17][C:16]=3[CH2:15]2)=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 57934200Tert-butyl[2-(4-formylphenoxy)-1,1-dimethylethyl]carbamateHCID 57934541pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 66627172(R)-6-{2-{[4-(2-Amino-2-methylpropoxy)benzyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 74.6%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (35 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 (32 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-8ebd19cb9c164b099c2b5f6f1a3cf69e
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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