Water → (3R,4R)-tert-butyl 3-azido-4-methoxypyrrolidine-1-carboxylate

HRID 339068Notes

Reaction equation

HRID 339068 reaction equation
[N:1]([C@H:4]1[C@H:8]([OH:9])[CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)=[N+:2]=[N-:3].[CH3:17]I.[H-].[Na+].O>CN(C=O)C.CCOCC>[N:1]([C@H:4]1[C@H:8]([O:9][CH3:17])[CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15855750Tert-butyl (3R,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 57349953(3R,4R)-tert-butyl 3-azido-4-methoxypyrrolidine-1-carboxylateYield 96.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (3R,4R)-tert-butyl 3-azido-4-hydroxypyrrolidine-1-carboxylate (2.00 g, 8.76 mmol) and MeI (1.64 mL, 26.3 mmol) in DMF (20 mL) was added 60% NaH (0.701 g, 17.5 mmol) at 0° C. The mixture was warmed to ambient temperature and stirred at ambient temperature for 1 hour. Water (20 mL) and ether (40 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1 hexane/ethyl acetate) to give (3R,4R)-tert-butyl 3-azido-4-methoxypyrrolidine-1-carboxylate (2.04 g, 96.1%) as thick oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f747cf198dc14f97b3e59492b696afc8
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…