Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312453, compound

HRID 1472901Notes

Reaction equation

HRID 1472901 reaction equation
C12CC(CC1)C=C2B(O)O.[F:11][C:12]1[C:13]([CH2:25][NH:26][C@H:27]([CH:30]([CH3:32])[CH3:31])[CH2:28][OH:29])=[N:14][C:15]([C:18]2[CH2:23][CH2:22][CH:21]([CH3:24])[CH2:20][CH:19]=2)=[CH:16][CH:17]=1>[Pd]>[F:11][C:12]1[C:13]([CH2:25][NH:26][C@H:27]([CH:30]([CH3:32])[CH3:31])[CH2:28][OH:29])=[N:14][C:15]([C:18]2[CH2:23][CH2:22][CH:21]([CH3:24])[CH2:20][CH:19]=2)=[CH:16][CH:17]=1.[F:11][C:12]1[C:13]([CH2:25][NH:26][C@H:27]([CH:30]([CH3:32])[CH3:31])[CH2:28][OH:29])=[N:14][C:15]([CH:18]2[CH2:19][CH2:20][CH:21]([CH3:24])[CH2:22][CH2:23]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 44119810Bicyclo[2.2.1]hept-2-en-2-ylboronic acidHCID 68312453HCID 68312453, compound

Product 2

HCID 68312453HCID 68312453, compoundHCID 68312465HCID 68312465, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(2R)-2-(((3-fluoro-6-(4-methylcyclohex-1-en-1-yl)pyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was prepared according to Example 199, substituting 4-methylcyclohex-1-enylboronic acid for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (2R)-2-(((3-fluoro-6-(4-methylcyclohex-1-en-1-yl)pyridin-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 309 (M+H)+.

Sources & evidence

ORD record
ord-f9bbb03f9a4e4054b4a433217d841664
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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