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

HRID 586716Notes

Reaction equation

HRID 586716 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].I[CH3:17].O>O1CCCC1>[CH3:17][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 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 12050278(S)-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 (3S)-N-tert-butoxycarbonylpyrrolidin-3-ol (U.S. Pat. No. 6,180,627 preparation 78), (12.5 g, 66.7 mmol) in tetrahydrofuran (330 ml), and the solution was stirred at room temperature for an hour. Iodomethane (14.5 g, 100 mmol) was then added and the reaction stirred for 18 hours. Water (100 ml) was added and the mixture concentrated under reduced pressure to remove the organic solvents. The solution was partitioned between water (750 ml) and ethyl acetate (750 ml) the layers separated, and the organic solution dried over magnesium sulphate and evaporated under reduced pressure to give the title compound.

Workup

  1. stirringthe reaction stirred for 18 hours
  2. concentrationthe mixture concentrated under reduced pressure
  3. customto remove the organic solvents
  4. customThe solution was partitioned between water (750 ml) and ethyl acetate (750 ml) the layers
  5. customseparated
  6. dry with materialthe organic solution dried over magnesium sulphate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7442498d7a094dbe891d013e61a65baf
Source dataset
uspto-grants-2005_08
Patent number
US06936619B2

Reaction notes

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