Triethylamine → HCID 25242003, compound

HRID 2099532Notes

Reaction equation

HRID 2099532 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.Br[CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[C:16]1([CH:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:4]2[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 236603BromodiphenylmethaneHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 25242003HCID 25242003, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

(3S)-3-Hydroxypyrrolidine (2.0 g) was dissolved in acetonitrile (10.0 mL) under cooling with ice. Triethylamine (4.8 mL) was added to the solution, and bromodiphenylmethane (5.7 g) in acetonitrile (10.0 mL) was added dropwise to the mixture, followed by stirring at room temperature for 4.5 hours. After completion of reaction, the insoluble material was removed through filtration, and water and toluene were added to the filtrate, whereby the organic layer was extracted. The formed aqueous layer was again extracted with toluene, and the organic layers were combined together, washed with saturated brine, and dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield crystalline residue. The residue was subjected to silica gel chromatography, to thereby give the target compound (5.2 g, yield 89.7%). The thus-obtained compound can be crystallized through treatment with hexane-ethyl acetate, alcohol-water, and so on.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added dropwise to the mixture
  3. customAfter completion of reaction
  4. customthe insoluble material was removed through filtration, and water and toluene
  5. additionwere added to the filtrate, whereby the organic layer
  6. extractionwas extracted
  7. extractionThe formed aqueous layer was again extracted with toluene
  8. washwashed with saturated brine
  9. dry with materialdried over sodium sulfate
  10. customThe drying agent was removed through filtration
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-44e8c28a4c7d4dfdbbbfea6b336ffea8
Source dataset
uspto-grants-2009_08
Patent number
US07569599B2

Reaction notes

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