benzyl (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine-1-carboxylate → (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine

HRID 81140Notes

Reaction equation

HRID 81140 reaction equation
[F:1][CH2:2][C@@H:3]1[CH2:7][C@@H:6]([O:8][CH3:9])[CH2:5][N:4]1C(OCC1C=CC=CC=1)=O.[H][H]>C(OCC)(=O)C.[Pd]>[F:1][CH2:2][C@@H:3]1[CH2:7][C@@H:6]([O:8][CH3:9])[CH2:5][NH:4]1

Participants

5

Reactant 2

HCID 86724496benzyl (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86724497(2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To benzyl (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine-1-carboxylate (529 mg, 1.98 mmol) dissolved in ethyl acetate (12.9 mL) was added palladium on carbon (211 mg, 0.2 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 (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine. 1H NMR (500 MHz, CDCl3) δ 4.44-4.19 (m, 2H), 3.29 (s, 3H), 3.09-2.93 (m, 2H), 2.02-1.92 (m, 1H), 1.78 (s, 2H), 1.62-1.56 (m, 1H), 1.25 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-9dde6d74d34b48fea2677eee48498144
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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