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

HRID 1615707Notes

Reaction equation

HRID 1615707 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-82c0fb6851484931af166a4bd85693f1
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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