Water → 2-chloro-1-[(3R)-3-fluoropyrrolidin-1-yl]ethanone

HRID 588570Notes

Reaction equation

HRID 588570 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[F:6][C@@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:1][CH2:2][C:3]([N:9]1[CH2:10][CH2:11][C@@H:7]([F:6])[CH2:8]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 27591633-Fluoropyrrolidine

Product 1

HCID 867172712-chloro-1-[(3R)-3-fluoropyrrolidin-1-yl]ethanoneYield 357.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloroacetyl chloride (632 μL, 7.94 mmol) was added dropwise to a solution of (3R)-3-fluoropyrrolidine (1 g, 7.94 mmol) and triethylamine (2.2 mL, 15.9 mmol) in CH2Cl2 (20 mL) at 5° C. The reaction mixture was stirred at room temperature for 1 h. Water and CH2Cl2 were added. The layers were separated and the aqueous was extracted with CH2Cl2. The combined organics were dried (MgSO4), filtered and concentrated in vacuo, to yield 2-chloro-1-[(3R)-3-fluoropyrrolidin-1-yl]ethanone (4.7 g).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with CH2Cl2
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a795e7e56bf84d41923f2e3e209e8f2d
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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