Water → HCID 18765923, compound

HRID 481014Notes

Reaction equation

HRID 481014 reaction equation
CC(C)([O-])C.[K+].[N:7]1([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][CH2:9][CH2:8]1.[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Br.O>C1COCC1.CCCCCC.C(OCC)(=O)C>[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][O:14][CH2:13][CH2:12][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

8

Reactant 4

HCID 962WaterHCID 762881-PyrrolidineethanolHCID 769652-Bromobenzyl bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 18765923HCID 18765923, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of potassium tert-butoxide (4.94 g, 44.0 mmol) in anhydrous THF (60 ml) was added dropwise a solution of 1-pyrrolidineethanol (5.07 g, 44.0 mmol) in anhydrous THF (20 ml) at 0° C. After 30 min at same temperature, to this was added dropwise a solution of 2-bromobenzyl bromide (10.0 g, 40.0 mmol) in anhydrous THF (20 ml) at 0° C. The reaction mixture was stirred at room temperature for 3 h. Water and 1:1 mixture of ethyl acetate and hexane were added to the reaction mixture and organic layer was separated. The organic layer was washed with water, brine and dried over sodium sulfate. After filtration, the filtrate was concentrated in vacuo to afford the titled compound (11.3 g, 99.3%) as a pale yellow oil.

Workup

  1. additionwere added to the reaction mixture and organic layer
  2. customwas separated
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-39fc8eda9af04dfa8e23969cb9152e4c
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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