Water → HCID 57554794, compound

HRID 1511872Notes

Reaction equation

HRID 1511872 reaction equation
Br[CH2:2][CH:3]([OH:7])[CH2:4][CH2:5]Br.[CH2:8]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CCOC(C)=O>[CH2:8]([C:16]1[CH:17]=[CH:18][C:19]([N:20]2[CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]2)=[CH:21][CH:22]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 295701,4-Dibromo-2-butanolHCID 853464-Octylaniline

Product 1

HCID 57554794HCID 57554794, compoundYield 537.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To 10 microwave vials were added 1,4-dibromobutan-2-ol (0.375 mL, 2.75 mmol), 4-octylaniline (0.572 mL, 2.5 mmol), potassium carbonate (0.380 g, 2.75 mmol) and water (3 mL). Each vial was heated in a CEM microwave at 100 watt, 120° C., 150 psi, ramp time 5 min and hold time 20 min. After cooling to room temperature EtOAc (1 mL) was added to each vial. After thorough mixing the organic layers were removed, combined and concentrated in vacuo. The product was purified by flash chromatography on silica gel (eluting with EtOAc/Hep) to provide 1-(4-octylphenyl)pyrrolidin-3-ol (3.7 g, 13.43 mmol, 53.7% yield) as a white solid which was stored under nitrogen in a sealed flask.

Workup

  1. customtime 20 min
  2. additionwas added to each vial
  3. additionAfter thorough mixing the organic layers
  4. customwere removed
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography on silica gel (eluting with EtOAc/Hep)

Sources & evidence

ORD record
ord-f81df46c328140729f2f077e4fa7fc37
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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