Triethylamine → Tert-butyl 2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate

HRID 1619295Notes

Reaction equation

HRID 1619295 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 550865tert-Butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 18007568Tert-butyl 2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylateYield 129.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (1.00 g, 4.97 mmol, 1.0 equiv) and Et3N (1.06 g, 10.5 mmol, 2.1 equiv) in DCM (15 mL) was added dropwise MsCl (0.85 g, 7.40 mmol, 1.5 equiv) at 0° C. Then the reaction mixture was stirred at room temperature for 3 h. After the mixture was washed with brine, the organic layer was separated, dried over Na2SO4, filtered, and concentrated to give 1.8 g of the crude product, which was used for the nest step without further purification.

Workup

  1. washAfter the mixture was washed with brine
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e87443b5247f4228afcbcb5824f11bc5
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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