Pyridine, hydrofluoride (1:1) → Methyl (1R,3R,4R)-3-fluoro-4-hydroxy-cyclopentanecarboxylate

HRID 1643416Notes

Reaction equation

HRID 1643416 reaction equation
[C@@H:1]12[O:6][C@@H:5]1[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]2.N1C=CC=CC=1.[FH:17]>ClC(Cl)C>[F:17][C@H:1]1[C@H:5]([OH:6])[CH2:4][C@@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 10374550(1R,3s,5S)-methyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate

Product 1

HCID 59178201Methyl (1R,3R,4R)-3-fluoro-4-hydroxy-cyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of methyl (1S,5R)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (300 mg, 2.110 mmol) in 3 ml of dichloroethane in a Teflon tube was added hydrogen fluoride-pyridine (0.190 ml, 2.110 mmol and allowed to stir at ambient for 6 hrs. Carefully poured onto 5 ml ice/NaHCO3 and extracted with three portions of DCM. Dried over sodium sulfate followed by Silica gel chromatgraphy with 30-50% Acetone-hexane to give title compound. 1H NMR (500 MHz, CDCl3) δ 1.96-2.03 (m, 1H), δ 2.12-2.32 (m, 3H), δ 2.38-2.52 (m, 1H), δ 3.12 (m, 1H), δ 3.72 (s, 3H), δ 4.34 (m, 1H), δ 4.86 (d of m, J=51.5 Hz, 1H)

Workup

  1. extractionextracted with three portions of DCM
  2. dry with materialDried over sodium sulfate

Sources & evidence

ORD record
ord-ffdae20c71604e77b138c1efbce78a62
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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