Water → (1S, 2R)-1-phenyl-2-hydroxymethylcyclopropane N,N-diethylcarboxamide

HRID 54045Notes

Reaction equation

HRID 54045 reaction equation
[C:1]1([C@:7]2(C(OC([C@@]3([C:22]4[CH:27]=CC=CC=4)C[C@H]3CO)=O)=O)[CH2:9][C@H:8]2[CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+:29].O.C(O[CH2:35][CH3:36])(=O)C.[O:37]1[CH2:41]CCC1>>[CH2:35]([N:29]([CH2:27][CH3:22])[CH:41]=[O:37])[CH3:36].[C:1]1([C@H:7]2[CH2:9][C@H:8]2[CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 131719977(1S, 2R)-1-phenyl-2-hydroxymethylcyclopropane carboxylic anhydride

Product 1

HCID 131719981(1S, 2R)-1-phenyl-2-hydroxymethylcyclopropane N,N-diethylcarboxamideYield 88%

Conditions

Temperature
-78 °C

Procedure

1.7 ml (16 mmol) of diethylamine was dissolved in 20 ml of anhydrous tetrahydrofuran. To the resultant solution was dropwise added 11 ml (16 mmol) of a solution of 1.64M butyllithium in hexane in a stream of argon gas at 0° C., to thereby obtain a solution of lithium diethylamine. To the obtained solution was dropwise added a solution of 1.7 g (10 mmol) of compound 25 obtained in Reference Example 17 in 20 ml of anhydrous tetrahydrofuran in a stream of argon gas at -78° C. to thereby obtain a mixture. Then, the obtained mixture was stirred at -78° C. for 2 hours to thereby effect a reaction. To the obtained mixture was added a saturated aqueous ammonium chloride solution to thereby terminate the reaction and then, the resultant mixture was subjected to distillation under reduced pressure to thereby remove the solvent and obtain a residue. Water was added to the obtained residue, and ethyl acetate was further added for extraction to obtain an organic layer. The organic layer was separated, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to thereby obtain a residue. The obtained residue was purified by silica gel column chromatography (the composition of the developing solvent was; ethyl acetate:hexane=1:1). As a result, compound 26 (yield: 88%) was obtained as a yellow oily product.

Workup

  1. customto thereby obtain a mixture
  2. customa reaction
  3. customto thereby terminate
  4. customthe reaction
  5. distillationthe resultant mixture was subjected to distillation under reduced pressure
  6. customto thereby remove the solvent
  7. customobtain a residue
  8. additionwas further added for extraction
  9. customto obtain an organic layer
  10. customThe organic layer was separated
  11. washwashed with saturated saline
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customto thereby obtain a residue
  15. customThe obtained residue was purified by silica gel column chromatography (the composition of the developing solvent

Sources & evidence

ORD record
ord-a1150d797d6d48c9992e82dd3b388c0e
Source dataset
uspto-grants-1997_04
Patent number
US05621142

Reaction notes

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