Cyclohexene oxide → rel-(1R,2R)-2-(1-Pyrrolidinyl)cyclohexanol

HRID 589419Notes

Reaction equation

HRID 589419 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6]12[O:12][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2>O>[N:1]1([C@@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9246Cyclohexene oxideHCID 31268Pyrrolidine

Product 1

HCID 10103566rel-(1R,2R)-2-(1-Pyrrolidinyl)cyclohexanolYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Pyrrolidine (4.26 g, 60 mmol) was added to a solution of cyclohexene oxide (1.96 g, 20 mmol) in H2O (6 mL), and the resulting mixture was heated at 90° C. for 16 hours. After cooling, the solvent was removed under reduced pressure and the resulting residue was extracted with DCM (10 mL×3). The organic phasew were combined and dried with anhydrous Na2SO4. After removing the Na2SO4 by filtration, the solvent was evaporated and the material dried under vacuum to afford the desired compound (+/−)-1 (3.3 g, 19.5 mmol, yield 98%). 1H NMR (CDCl3) δ 4.06 (s, 1H), 3.45-3.30 (m, 1H), 2.75-2.63 (m, 2H), 2.62-2.50 (m, 2H), 2.51-2.42 (m, 1H), 1.90-1.58 (m, 8H), 1.45-1.15 (m, 4H).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. extractionthe resulting residue was extracted with DCM (10 mL×3)
  4. dry with materialdried with anhydrous Na2SO4
  5. customAfter removing the Na2SO4
  6. filtrationby filtration
  7. customthe solvent was evaporated
  8. customthe material dried under vacuum

Sources & evidence

ORD record
ord-c2c926ca4e4d45af9dfb774d48d92523
Source dataset
uspto-grants-2016_01
Patent number
US09233168B2

Reaction notes

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