benzyl (2R)-5-methoxy-2-methylpiperidine-1-carboxylate → (2R)-5-methoxy-2-methylpiperidine

HRID 81148Notes

Reaction equation

HRID 81148 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][N:7](C(OCC2C=CC=CC=2)=O)[C@H:6]([CH3:19])[CH2:5][CH2:4]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][CH:3]1[CH2:8][NH:7][C@H:6]([CH3:19])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 86724501benzyl (2R)-5-methoxy-2-methylpiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86724502(2R)-5-methoxy-2-methylpiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To benzyl (2R)-5-methoxy-2-methylpiperidine-1-carboxylate (345 mg, 1.31 mmol) dissolved in ethyl acetate (6.5 mL) was added palladium on carbon (139 mg, 0.13 mmol). Hydrogen gas was added via balloon, and the reaction was stirred at room temperature for 3 hours. The mixture was filtered over celite and concentrated under reduced pressure to afford (2R)-5-methoxy-2-methylpiperidine. 1H NMR (500 MHz, DMSO-d6) δ 3.33 (s, 3H), 3.23-3.13 (m, 2H), 2.66-2.59 (m, 1H), 2.03-1.97 (m, 1H), 1.47-1.40 (m, 1H), 1.39-1.28 (m, 2H), 1.08-1.04 (m, 3H), 0.91-0.79 (m, 2H).

Workup

  1. filtrationThe mixture was filtered over celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da68e188e1184401a1155ec3ec4d1575
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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