Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312568, compound

HRID 1472910Notes

Reaction equation

HRID 1472910 reaction equation
C12CC(CC1)C=C2B(O)O.[C:11]1([C:16]2[N:21]=[C:20]([CH2:22][NH:23][C@H:24]([CH:27]([CH3:29])[CH3:28])[CH2:25][OH:26])[C:19]([F:30])=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][CH:12]=1>[Pd]>[C:11]1([C:16]2[N:21]=[C:20]([CH2:22][NH:23][C@H:24]([CH:27]([CH3:28])[CH3:29])[CH2:25][OH:26])[C:19]([F:30])=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][CH:12]=1.[CH:11]1([C:16]2[N:21]=[C:20]([CH2:22][NH:23][C@H:24]([CH:27]([CH3:28])[CH3:29])[CH2:25][OH:26])[C:19]([F:30])=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 44119810Bicyclo[2.2.1]hept-2-en-2-ylboronic acidHCID 68312568HCID 68312568, compound

Product 2

HCID 68312568HCID 68312568, compoundHCID 68312698HCID 68312698, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-2-(((6-(cyclopent-1-en-1-yl)-3-fluoropyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was prepared according to Example 199, substituting 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (R)-2-(((6-(cyclopent-1-en-1-yl)-3-fluoropyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was subjected to hydrogenation (H2 atmosphere, Pd/C catalyst) to provide the title compound. MS (ESI+) m/z 281 (M+H)+.

Sources & evidence

ORD record
ord-43bee7512e4348e683e455a09328cea7
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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