Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312509, compound

HRID 1472902Notes

Reaction equation

HRID 1472902 reaction equation
C12CC(CC1)C=C2B(O)O.[CH2:11]([CH:13]1[CH2:18][CH2:17][C:16]([C:19]2[N:24]=[C:23]([CH2:25][NH:26][C@H:27]([CH:30]([CH3:32])[CH3:31])[CH2:28][OH:29])[C:22]([F:33])=[CH:21][CH:20]=2)=[CH:15][CH2:14]1)[CH3:12]>[Pd]>[CH2:11]([CH:13]1[CH2:18][CH2:17][C:16]([C:19]2[N:24]=[C:23]([CH2:25][NH:26][C@H:27]([CH:30]([CH3:32])[CH3:31])[CH2:28][OH:29])[C:22]([F:33])=[CH:21][CH:20]=2)=[CH:15][CH2:14]1)[CH3:12].[CH2:11]([CH:13]1[CH2:14][CH2:15][CH:16]([C:19]2[N:24]=[C:23]([CH2:25][NH:26][C@H:27]([CH:30]([CH3:32])[CH3:31])[CH2:28][OH:29])[C:22]([F:33])=[CH:21][CH:20]=2)[CH2:17][CH2:18]1)[CH3:12]

Participants

5

Reactant 2

HCID 44119810Bicyclo[2.2.1]hept-2-en-2-ylboronic acidHCID 68312509HCID 68312509, compound

Product 2

HCID 68312509HCID 68312509, compoundHCID 68312693HCID 68312693, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(2R)-2-(((6-(4-ethylcyclohex-1-en-1-yl)-3-fluoropyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was prepared according to Example 199, substituting 2-(4-ethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (2R)-2-(((6-(4-ethylcyclohex-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 323 (M+H)+.

Sources & evidence

ORD record
ord-b6e110a00a3e422593fcef1ae04df188
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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