Diisopropylethylamine → 4-{3-[1-(3,5-Diisopropoxy-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenoxy}-butyric acid methyl ester

HRID 502432Notes

Reaction equation

HRID 502432 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([C:14](=[O:22])[NH:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:11]=[C:10]([O:23][CH3:24])[CH:9]=1.[CH:26]([O:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([O:38][CH:39]([CH3:41])[CH3:40])[CH:37]=1)[CH:33]=O)([CH3:28])[CH3:27].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([O:23][CH3:24])[CH:11]=[C:12]([C:14](=[O:22])[NH:15][CH:16]2[CH2:17][CH2:18][N:19]([CH2:33][C:32]3[CH:35]=[C:36]([O:38][CH:39]([CH3:41])[CH3:40])[CH:37]=[C:30]([O:29][CH:26]([CH3:28])[CH3:27])[CH:31]=3)[CH2:20][CH2:21]2)[CH:13]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 113106053,5-DiisopropoxybenzaldehydeHCID 684579394-[3-Methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-butyric acid methyl ester

Product 1

HCID 684586984-{3-[1-(3,5-Diisopropoxy-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenoxy}-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 4-[3-methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-butyric acid methyl ester (example 168b) was reacted with 3,5-diisopropoxy-benzaldehyde (example 126b), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless oil. MS: 557.3 (MH+).

Sources & evidence

ORD record
ord-67fc14b7943c4055997df555517ac304
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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