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

HRID 538452Notes

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-2b67cd4fd48b46779c75e1abd811e127
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865717B2

Reaction notes

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