Potassium Carbonate → HCID 57554655, compound

HRID 1511854Notes

Reaction equation

HRID 1511854 reaction equation
[NH2:1][C@:2]1([CH2:15][OH:16])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[CH2:3]1.[C:17]([O-])([O-])=[O:18].[K+].[K+]>C(=O)(OCC)OCC>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C@@H:4]2[CH2:5][CH2:6][C@@:2]3([NH:1][C:17](=[O:18])[O:16][CH2:15]3)[CH2:3]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 24997390HCID 24997390, compound

Product 1

HCID 57554655HCID 57554655, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 7766Diethyl CarbonateSolvent

Procedure

To a suspension of [(1R,3R)-1-amino-3-(4-methoxy-phenyl)-cyclopentyl]-methanol (6.70 g, 30.3 mmol) in diethyl carbonate was added K2CO3 (4.83 g, 35.0 mmol) and the mixture was heated at reflux for about 20 hours. The reaction was concentrated, taken up in EtOAc (150 mL), washed with water (75 mL), dried over Na2SO4, filtered and concentrated. The crude product was further purified via flash chromatography with a gradient of from 40% to 80% EtOAc in heptane. Pure fractions were combined and concentrated to yield 5.99 g (80%) of (5R,7R)-7-(4-methoxy-phenyl)-3-oxa-1-aza-spiro[4.4]nonan-2-one as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for about 20 hours
  3. concentrationThe reaction was concentrated
  4. washwashed with water (75 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was further purified via flash chromatography with a gradient of from 40% to 80% EtOAc in heptane
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-373ee7c8194947d6bef220c99072e68d
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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