Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312496, compound

HRID 1472906Notes

Reaction equation

HRID 1472906 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[CH2:19][C:20]3([CH2:25][CH2:26][CH:27]=2)[O:24][CH2:23][CH2:22][O:21]3)=[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[CH2:19][C:20]3([CH2:25][CH2:26][CH:27]=2)[O:24][CH2:23][CH2:22][O:21]3)=[CH:16][CH:17]=1.[O:21]1[C:20]2([CH2:25][CH2:26][CH2:27][CH:18]([C:15]3[N:14]=[C:13]([CH2:28][NH:29][C@H:30]([CH:33]([CH3:34])[CH3:35])[CH2:31][OH:32])[C:12]([F:11])=[CH:17][CH:16]=3)[CH2:19]2)[O:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 44119810Bicyclo[2.2.1]hept-2-en-2-ylboronic acidHCID 68312928HCID 68312928, compound

Product 2

HCID 68312496HCID 68312496, compoundHCID 68312928HCID 68312928, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-2-(((3-fluoro-6-(1,4-dioxaspiro[4.5]dec-7-en-7-yl)pyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was prepared according to Example 199, substituting 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-7-yl)-1,3,2-dioxaborolane for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (R)-2-(((3-fluoro-6-(1,4-dioxaspiro[4.5]dec-7-en-7-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 353 (M+H)+.

Sources & evidence

ORD record
ord-29b29f47b56b4df29f84577b647e96f4
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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