Methyl iodide → HCID 68984554, compound

HRID 748630Notes

Reaction equation

HRID 748630 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([F:23])[CH:15]=2)[CH2:10][CH:9]1[CH2:24][OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26]I.[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([F:23])[CH:15]=2)[CH2:10][CH:9]1[CH2:24][O:25][CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68982736HCID 68982736, compound

Product 1

HCID 68984554HCID 68984554, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 22.7 g of 4-(3-fluoro-5-nitrophenoxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (6), 250 mL of anhydrous DMF, and 36.3 g of MeI at 0° C. was added 3.9 g of 60% NaH, in several portions. The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated to remove excess MeI then diluted with H2O. The mixture was diluted with 500 mL of saturated NH4Cl and extracted 3 times with 500 mL of EtOAc. The combined organic layers were dried and concentrated to yield 23 g of 4-(3-fluoro-5-nitro-phenoxy)-2-methoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (7).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove excess MeI
  3. additionthen diluted with H2O
  4. additionThe mixture was diluted with 500 mL of saturated NH4Cl
  5. extractionextracted 3 times with 500 mL of EtOAc
  6. customThe combined organic layers were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-516c79255bbd4437acd1c25cbbc1a6c4
Source dataset
uspto-grants-2008_07
Patent number
US07399866B2

Reaction notes

Loading…