Triethylamine → HCID 58483968, compound

HRID 81393Notes

Reaction equation

HRID 81393 reaction equation
[F:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:4]([CH2:14][OH:15])[CH2:3]1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[F:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@@H:4]([CH2:14][O:15][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58483823tert-Butyl (2R,4S)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 58483968HCID 58483968, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

7.5 3.2 g of tert-butyl (2R,4S)-4-fluoro-2-hydroxymethylpyrrolidine-1-carboxylate are dissolved in 50 ml of CH2Cl2 with stirring, 3.1 ml of triethylamine are added, the mixture is cooled to 0-5° C., and a solution of 1.4 ml of methane-sulfonyl chloride in 10 ml of CH2Cl2 is subsequently added dropwise. The mixture is subsequently stirred at RT for 4 h. After aqueous work-up, the 4.1 g of tert-butyl (2R,4S)-4-fluoro-2-methanesulfonyloxymethylpyrrolidine-1-carboxylate) obtained are reacted further directly.

Workup

  1. stirringThe mixture is subsequently stirred at RT for 4 h

Sources & evidence

ORD record
ord-983190d0194e4829bd268b898157d838
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Reaction notes

Loading…