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

HRID 1950206Notes

Reaction equation

HRID 1950206 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C@@H: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(OC(=O)[NH:35][C:36]([CH3:48])([CH3:47])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]=O)=[CH:41][CH:40]=1)(C)(C)C>>[NH2:35][C:36]([CH3:48])([CH3:47])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:2][CH2:1][NH:3][C:4]2[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=2[C@@H:12]2[CH2:21][CH2:20][C:19]3[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=3[CH2:13]2)=[CH:41][CH:40]=1

Participants

3

Reactant 2

HCID 57934200Tert-butyl[2-(4-formylphenoxy)-1,1-dimethylethyl]carbamateHCID 57934253HCID 57934253, compound

Product 1

HCID 66627047(R)-6-{2-{[4-(2-Amino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 36.5%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (33 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 (15 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-eadab12a7d81436c84d2e32e8a4e489d
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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