tert-Butyl 4-(7-fluorobenzofuran-2-yl)-4-hydroxypiperidine-1-carboxylate → tert-Butyl 4-(7-fluoro-2,3-dihydrobenzofuran-2-yl)-4-hydroxypiperidine-1-carboxylate

HRID 1025491Notes

Reaction equation

HRID 1025491 reaction equation
[F:1][C:2]1[C:10]2[O:9][C:8]([C:11]3([OH:24])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[F:1][C:2]1[C:10]2[O:9][CH:8]([C:11]3([OH:24])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67468840tert-Butyl 4-(7-fluorobenzofuran-2-yl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 67468828tert-Butyl 4-(7-fluoro-2,3-dihydrobenzofuran-2-yl)-4-hydroxypiperidine-1-carboxylateYield 77.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a degassed solution of tert-butyl 4-(7-fluorobenzofuran-2-yl)-4-hydroxypiperidine-1-carboxylate (0.52 g, 1.55 mmol) in EtOH (9.62 mL) was added 10% Pd—C (0.495 g, 0.465 mmol). Upon completion of addition, the reaction mixture was charged with 55 psi of H2 overnight. After the conclusion of this period, the Pd—C was filtered off through a pad of CELITE®, and the filter cake was rinsed with EtOH. The solvent was removed under reduced pressure to afford Compound 1E as a light yellow solid (0.404 g, 77% yield).

Workup

  1. additionUpon completion of addition
  2. additionthe reaction mixture was charged with 55 psi of H2 overnight
  3. filtrationAfter the conclusion of this period, the Pd—C was filtered off through a pad of CELITE®
  4. washthe filter cake was rinsed with EtOH
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f1719f36922d4b869d4b8b4d8431d1b5
Source dataset
uspto-grants-2014_05
Patent number
US08729084B2

Reaction notes

Loading…