Triethylamine → (2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate

HRID 631762Notes

Reaction equation

HRID 631762 reaction equation
[OH:1][C@@H:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[Br:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:20](Cl)=[O:21]>ClCCCl.O>[Br:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:20]([O:1][C@@H:2]([CH3:10])[C:3](=[O:4])[N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11051776(2S)-2-hydroxy-1-(1-pyrrolidinyl)-1-propanoneHCID 12575778Bromo-4-chlorophenylacetyl chloride

Product 1

HCID 42644107(2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetateYield 59%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of (2S)-2-hydroxy-1-(pyrrolidin-1-yl)propan-1-one (24.0 g, 0.17 mol) in DCE (120 mL) was added triethylamine (84.69 g, 0.84 mol) and 2-bromo-2-(4-chlorophenyl)acetyl chloride (crude, 46.29 g, 0.17 mol) at 0° C. The reaction mixture was stirred for 2 h at RT. The reaction mixture was diluted with water (200 mL) and separated the organic layer. The organic layer was washed with 10% NaS2O3 (100 mL) and saturated sodium bicarbonate (60 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude residue was purified by flash column on 100-200 mesh silica-gel (20-25% ethyl acetate-hexane) to afford (2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate 4 (37.5 g, 59%) as brown sticky gum.

Workup

  1. customseparated the organic layer
  2. washThe organic layer was washed with 10% NaS2O3 (100 mL) and saturated sodium bicarbonate (60 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by flash column on 100-200 mesh silica-gel (20-25% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-acf81ffc1af64838a48ecd215fbe61ec
Source dataset
uspto-grants-2016_04
Patent number
US09321716B1

Reaction notes

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