Acetic Acid → (1S,3R)-3-(3-pyridyl)cyclopentyl acetate

HRID 655163Notes

Reaction equation

HRID 655163 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:11][CH2:10][C@@H:9]([OH:12])[CH2:8]2)[CH:2]=1.[C:13](O)(=[O:15])[CH3:14].CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOC(C)=O>[C:13]([O:12][C@H:9]1[CH2:10][CH2:11][C@@H:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:8]1)(=[O:15])[CH3:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59486143(1R,3R)-3-(3-pyridyl)cyclopentanol

Product 1

HCID 59486131(1S,3R)-3-(3-pyridyl)cyclopentyl acetateYield 100.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1R,3R)-3-(3-pyridyl)cyclopentanol (3.47 g, 21.3 mmol) in THF (100 mL) was cooled to 4° C. and treated with acetic acid (1.34 mL, 23.4 mmol), Diisopropylazodicarboxylate (4.61 mL, 23.4 mmol) and triphenylphosphine (6.14 g, 23.4 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with EtOAc, and washed with H2O and brine. The organic layers was dried over Na2SO4. After concentration under reduced pressure, the residue was purified by column chromatography (NH, Hexane/EtOAc=6/1) to yield (1S,3R)-3-(3-pyridyl)cyclopentyl acetate (4.39 g, 100%) as colorless oil.

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic layers was dried over Na2SO4
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by column chromatography (NH, Hexane/EtOAc=6/1)

Sources & evidence

ORD record
ord-af09548d6c284a588d17147126956e50
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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