Benzyl cyclopent-3-enecarboxylate → Benzyl 3-hydroxycyclopentanecarboxylate

HRID 1160611Notes

Reaction equation

HRID 1160611 reaction equation
[CH:1]1([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.B1([O-])O[O:17]1.O.O.O.O.[Na+]>C1COCC1>[OH:17][CH:3]1[CH2:4][CH2:5][CH:1]([C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH2:2]1

Participants

4

Reactant 2

HCID 22084261Benzyl cyclopent-3-enecarboxylateHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 14530758Benzyl 3-hydroxycyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The benzyl cyclopent-3-ene-1-carboxylate (2.0 g, 9.89 mmol) was dissolved in 20 mL of THF and cooled to 0° C. under nitrogen. Borane-THF complex (0.95 mL, 9.89 mmol) was added via syringe and the mixture was stirred for 30 minutes at 0° C. Sodium perborate tetrahydrate solution (100 mL of 0.33 M aqueous solution) was added, and after 30 minutes the reaction mixture was extracted with ethyl acetate. The combined extracts were washed with water and brine and then dried over sodium sulfate. Filtration and concentration provided the crude product which was purified by chromatography on silica gel eluting with 10 to 30% EtOAc in hexanes to provide benzyl 3-hydroxycyclopentanecarboxylate.

Workup

  1. additionBorane-THF complex (0.95 mL, 9.89 mmol) was added via syringe
  2. extractionafter 30 minutes the reaction mixture was extracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration
  6. customprovided the crude product which
  7. customwas purified by chromatography on silica gel eluting with 10 to 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-8d292544f4b64ee49c924bd93fb0e600
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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