Water → (R)-tert-Butyl 3-methoxypyrrolidine-1-carboxylate

HRID 1829183Notes

Reaction equation

HRID 1829183 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][C@@H:12]([OH:15])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:16]I.O>O1CCCC1>[CH3:16][O:15][C@@H:12]1[CH2:13][CH2:14][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 34179484(R)-tert-Butyl 3-methoxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (2.2 g, 80% dispersion in mineral oil, 73.2 mmol) was added to an ice-cooled solution of (3R)-N-tert-butoxycarbonylpyrrolidin-3-ol (J. Med. Chem. 41; 25; 1998; 4983) (12.5 g, 66.7 mmol) in tetrahydrofuran (330 ml), and the solution stirred at room temperature for an hour. Methyl iodide (14.5 g, 100 mmol) was then added and the reaction stiired for 18 hours. Water (100 ml) was added and the mixture concentrated under reduced pressure to remove the organic solvents. The aqueous was extracted with ethyl acetate, the combined organic solutions dried (MgSO4) and evaporated under reduced pressure to give the title compound as an oil, 12.48 g.

Workup

  1. concentrationthe mixture concentrated under reduced pressure
  2. customto remove the organic solvents
  3. extractionThe aqueous was extracted with ethyl acetate
  4. dry with materialthe combined organic solutions dried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b9da6097562e455993d688086819fce8
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

Loading…