Isopropanol → Tert-butyl 4-(4-cyanobenzyl)-4-hydroxypiperidine-1-carboxylate

HRID 60576Notes

Reaction equation

Br[C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2([OH:20])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(O)C.C[C:34]([N:36](C)C)=O>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:34]([C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2([OH:20])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1)#[N:36]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl 4-(4-bromobenzyl)-4-hydroxypiperidine-1-carboxylate (35 g), K4Fe(CN)6 (12 g), palladium(II) acetate (1.1 g), sodium carbonate (11 g), 2-propanol (7.5 mL) and DMA (150 mL) was stirred at 120° C. for 12 hr. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane, and filtered through celite. The filtrate was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (17 g).

Workup

temperatureto cool to room temperature
filtrationfiltered through celite
washThe filtrate was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c0d5ad506db64d0da6ecdcea92fb6e60
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440990B2

Reaction notes

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