Methyl iodide → N-BOC-3(R)-methoxy-(L)-proline, methyl ester

HRID 496238Notes

Reaction equation

HRID 496238 reaction equation
[C:1]([N:8]1[CH2:16][CH2:15][C@@H:14]([OH:17])[C@H:9]1[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:18]I>CN(C=O)C>[C:1]([N:8]1[CH2:16][CH2:15][C@@H:14]([O:17][CH3:18])[C@H:9]1[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 109885451,2-Pyrrolidinedicarboxylic acid, 3-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,3S)-rel-

Product 1

HCID 66619640N-BOC-3(R)-methoxy-(L)-proline, methyl esterYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg (2.05 mmol) of N-BOC-3(R)-hydroxy-(L)-proline, methyl ester and 1.7 g (12.2 mmol) of MeI in 10 mL of DMF was added 473 mg (2.05 mmol) of Ag2O. The mixture was stirred for 18 h and was then filtered through a pad of celite and concentrated. The crude residue was dissolved in EtOAc and washed with 1M HCl (2×10 mL), saturated NaHCO3 (2×10 mL), brine (1×10 mL), dried anhydrous MgSO4, and concentrated to give 500 mg of N-BOC-3(R)-methoxy-(L)-proline, methyl ester as a light yellow oil which was used without further purification.

Workup

  1. filtrationwas then filtered through a pad of celite
  2. concentrationconcentrated
  3. dissolutionThe crude residue was dissolved in EtOAc
  4. washwashed with 1M HCl (2×10 mL), saturated NaHCO3 (2×10 mL), brine (1×10 mL), dried anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d5da4b881a2e45be924d91c64f08c5ad
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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