Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312431, compound

HRID 1472907Notes

Reaction equation

HRID 1472907 reaction equation
C12CC(CC1)C=C2B(O)O.[F:11][C:12]1[C:13]([CH2:28][NH:29][C@H:30]([CH:33]([CH3:35])[CH3:34])[CH2:31][OH:32])=[N:14][C:15]([C:18]2[CH2:23][CH2:22][CH:21]([C:24]([F:27])([F:26])[F:25])[CH2:20][CH:19]=2)=[CH:16][CH:17]=1>[Pd]>[F:11][C:12]1[C:13]([CH2:28][NH:29][C@H:30]([CH:33]([CH3:35])[CH3:34])[CH2:31][OH:32])=[N:14][C:15]([C:18]2[CH2:23][CH2:22][CH:21]([C:24]([F:27])([F:25])[F:26])[CH2:20][CH:19]=2)=[CH:16][CH:17]=1.[F:11][C:12]1[C:13]([CH2:28][NH:29][C@H:30]([CH:33]([CH3:35])[CH3:34])[CH2:31][OH:32])=[N:14][C:15]([CH:18]2[CH2:23][CH2:22][CH:21]([C:24]([F:27])([F:25])[F:26])[CH2:20][CH2:19]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 44119810Bicyclo[2.2.1]hept-2-en-2-ylboronic acidHCID 68312606HCID 68312606, compound

Product 2

HCID 68312431HCID 68312431, compoundHCID 68312606HCID 68312606, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(2R)-2-(((3-fluoro-6-(4-(trifluoromethyl)cyclohex-1-en-1-yl)pyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was prepared according to Example 199, substituting 4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)cyclohex-1-enyl)-1,3,2-dioxaborolane for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (2R)-2-(((3-fluoro-6-(4-(trifluoromethyl)cyclohex-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 363 (M+H)+.

Sources & evidence

ORD record
ord-06ba87c20a83456fa14b547686e51b3d
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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