Lithium Bromide → tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate

HRID 1789891Notes

Reaction equation

HRID 1789891 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13]OS(C(F)(F)F)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[Br-:23]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][Br:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 53385508tert-Butyl 3-((((trifluoromethyl)sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 24730280tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-trifluoromethanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (3.85 g, 13.8 mmol) and LiBr (3.61 g, 42 mmol) in dry acetone (30 mL) was refluxed overnight. The reaction mixture was allowed to cool to room temperature, filtered and concentrated. The residue was dissolved in CH2Cl2 and washed with water, dried and concentrated under reduced pressure to give 6 g of the crude product. Purification by flash chromatography (Heptane/EtOAc: 1/0→68/32) afforded of 3-bromomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (2.84 g, 78%) as a colourless oil.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give 6 g of the crude product
  9. customPurification by flash chromatography (Heptane/EtOAc: 1/0→68/32)

Sources & evidence

ORD record
ord-beace4a3209f4a8ebfd648ef8b15f3c8
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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