Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312351, compound

HRID 1472904Notes

Reaction equation

HRID 1472904 reaction equation
C12CC(CC1)C=C2B(O)O.[F:11][C:12]1([F:33])[CH2:17][CH2:16][C:15]([C:18]2[N:23]=[C:22]([CH2:24][NH:25][C@H:26]([CH:29]([CH3:31])[CH3:30])[CH2:27][OH:28])[C:21]([F:32])=[CH:20][CH:19]=2)=[CH:14][CH2:13]1>[Pd]>[F:33][C:12]1([F:11])[CH2:17][CH2:16][C:15]([C:18]2[N:23]=[C:22]([CH2:24][NH:25][C@H:26]([CH:29]([CH3:30])[CH3:31])[CH2:27][OH:28])[C:21]([F:32])=[CH:20][CH:19]=2)=[CH:14][CH2:13]1.[F:33][C:12]1([F:11])[CH2:17][CH2:16][CH:15]([C:18]2[N:23]=[C:22]([CH2:24][NH:25][C@H:26]([CH:29]([CH3:30])[CH3:31])[CH2:27][OH:28])[C:21]([F:32])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 44119810Bicyclo[2.2.1]hept-2-en-2-ylboronic acidHCID 68312351HCID 68312351, compound

Product 2

HCID 68312351HCID 68312351, compoundHCID 68312506HCID 68312506, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-2-(((6-(4,4-difluorocyclohex-1-en-1-yl)-3-fluoropyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was prepared according to Example 199, substituting 2-(4,4-difluorocyclohex-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (R)-2-(((6-(4,4-difluorocyclohex-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 331 (M+H)+.

Sources & evidence

ORD record
ord-a84788e5d4684c18b2ebc7bd5188a54a
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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