Sodium Carbonate → HCID 54573355, compound

HRID 338976Notes

Reaction equation

[F:1][CH2:2][C:3]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6][NH:5][CH2:4]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>O1CCOCC1.O>[F:1][CH2:2][C:3]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6][N:5]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:4]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 3-(fluoromethyl)pyrrolidine-3-carboxylate (1.86 g, 10.62 mmol) in a 1:1 mixture of 1,4-dioxane/water (18 mL) was added sodium carbonate (1.35 g, 12.74 mmol) and the mixture cooled to 0° C. in an ice bath. Benzyl chloroformate (1.79 mL, 12.74 mmol) was added dropwise and the resulting mixture was stirred at 0° C. for 30 minutes, then at ambient temperature for 18 hours. The mixture was partitioned between water and ether, and the layers separated. The organic layer was washed sequentially with water, saturated sodium bicarbonate solution and brine, then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by chromatography (Biotage 25M; 15% ethyl acetate/hexanes) to afford 1-benzyl 3-ethyl 3-(fluoromethyl)pyrrolidine-1,3-dicarboxylate (3.3 g, 100%).

Workup

waitat ambient temperature for 18 hours
customThe mixture was partitioned between water and ether
customthe layers separated
washThe organic layer was washed sequentially with water, saturated sodium bicarbonate solution and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography (Biotage 25M; 15% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-6464279f856646f5bce9540ac7872dd4
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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