Sodium Hydroxide → rac-(1R*,2R*,4R*)-2-(2-hydroxy-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

HRID 220291Notes

Reaction equation

HRID 220291 reaction equation
C([O:5][C:6](=O)[CH2:7][C:8]1([OH:22])[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[OH:5][CH2:6][CH2:7][C:8]1([OH:22])[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 77200910HCID 77200910, compound

Product 1

HCID 68412881rac-(1R*,2R*,4R*)-2-(2-hydroxy-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-olYield 109.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

295 mg of rac-(1R*,2R*,4R*)-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid tert.-butyl ester (intermediate K1A, major racemate) were dissolved in 6 mL THF and cooled to −15° C. To this solution were added dropwise 1.65 mL of a LiAlH4 solution (2.3M in THF). After complete addition the reaction mixture was allowed to warm to 0° C. over 3 h. Under cooling 1M aq. NaOH was added dropwise. The mixture was diluted with THF, filtrated over a pad of celite, washed with THF, EtOAc. The filtrate was evaporated to dryness to give 0.25 g of rac-(1R*,2R*,4R*)-2-(2-hydroxy-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol as white solid.

Workup

  1. additionAfter complete addition the reaction mixture
  2. temperatureto warm to 0° C. over 3 h
  3. additionwas added dropwise
  4. filtrationfiltrated over a pad of celite
  5. washwashed with THF, EtOAc
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f088dd51745e46eea7a723e72e46bb30
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

Loading…