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

HRID 717270Notes

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-9595c1b2d1f84bb4843a4412c1045c63
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193709B2

Reaction notes

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