Triphenylphosphine → tert-Butyl 4-(2-(5-bromo-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)piperidine-1-carboxylate

HRID 517972Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5]([OH:8])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:33][CH2:34][CH:35]1[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:10])[F:11])[C:5]([O:8][CH2:33][CH2:34][CH:35]2[CH2:36][CH2:37][N:38]([C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42])[CH2:39][CH2:40]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 5-bromo-2-hydroxy-3-(trifluoromethyl)pyridine (6.90 g) in 1,4-dioxane (100 ml), triphenylphosphine (9.44 g) and tert-butyl 4-(2-hydroxyethyl)-piperidine-1-carboxylate (7.41 g) were added. Then diisopropyl azodicarboxylate (DIAD, 7.52 ml, 7.67 g) was added dropwise and stirred at 20° C. for 18 h. Solvent was then removed under reduced pressure and residue purified by Biotage SNAP cartridge KP-Sil column (340 g, hepane:ethyl acetate=1:0, 5:1 to 4:1) to give 9.0 g orange oil as tert-butyl 4-(2-(5-bromo-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)-piperidine-1-carboxylate (70%).

Workup

additionwere added
customSolvent was then removed under reduced pressure and residue
custompurified by Biotage SNAP cartridge KP-Sil column (340 g, hepane:ethyl acetate=1:0, 5:1 to 4:1)

Sources & evidence

ORD record: ord-0c33095b22c44370b44da9dd3585948a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115126B2

Reaction notes

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