4-Methylpiperidin-4-ol → (Rac)-5-(4-hydroxy-4-methyl-piperidin-1-yl)-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-pentanoic acid methyl ester

HRID 1096228Notes

Reaction equation

HRID 1096228 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([N:9]1[C:15](=[O:16])[CH2:14][CH2:13][N:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH2:11][CH2:10]1)[CH2:5][CH2:6][CH2:7]Br.[CH3:28][C:29]1([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[CH3:1][O:2][C:3](=[O:27])[CH:4]([N:9]1[C:15](=[O:16])[CH2:14][CH2:13][N:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH2:11][CH2:10]1)[CH2:5][CH2:6][CH2:7][N:32]1[CH2:33][CH2:34][C:29]([OH:35])([CH3:28])[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 156491744-Methylpiperidin-4-ol2×HCID 66783116(Rac)-5-bromo-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-pentanoic acid methyl ester

Product 1

HCID 59159271(Rac)-5-(4-hydroxy-4-methyl-piperidin-1-yl)-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-pentanoic acid methyl esterYield 73%

Procedure

In analogy to the procedure described in example 25B, (rac)-5-bromo-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-pentanoic acid methyl ester (example 26A) and 4-methyl-piperidin-4-ol (intermediate 8) gave the title compound in 73% yield as colorless oil. MS: 486.3 (MH+).

Sources & evidence

ORD record
ord-3bd2286e23284b57b5bd8fbb0a8bb610
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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