Triethylamine → HCID 54147914, compound

HRID 975687Notes

Reaction equation

HRID 975687 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][C:14]#[N:15])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:9][C@H:8]1[CH2:13][C:14]#[N:15])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54567783HCID 54567783, compound

Product 1

HCID 54147914HCID 54147914, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-2-cyanomethyl-4-hydroxypyrrolidine (2.95 g) in dichloromethane (30 ml) were added triethylamine (1.85 g) and a solution of methanesulfonyl chloride (1.76 g) in dichloromethane (2 ml) at ice-cooling. After stirring at 5°-10° C. for 1 hour, the solution was poured into an ice water. The separated organic layer was washed with water and aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and evaporated to give (2R,4R)-1-allyloxycarbonyl-2-cyanomethyl-4-methanesulfonyloxypyrrolidine (4.44 g).

Workup

  1. washThe separated organic layer was washed with water and aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-c0c4affecd8c4d19a65675f6821a8a38
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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