Sodium Hydroxide → (R)-4-hydroxy-2-(3-benzyloxybenzyl)cyclopent-2-enone

HRID 1803640Notes

Reaction equation

HRID 1803640 reaction equation
C([O:4][C@@H:5]1[CH2:9][C:8](=[O:10])[C:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)=[CH:6]1)(=O)C.[OH-].[Na+]>OP([O-])(O)=O.[K+].OP(O)(O)=O>[OH:4][C@@H:5]1[CH2:9][C:8](=[O:10])[C:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)=[CH:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71170042(R)-3-(3-benzyloxybenzyl)-4-oxocyclopent-2-enyl acetate2×

Product 1

HCID 71170047(R)-4-hydroxy-2-(3-benzyloxybenzyl)cyclopent-2-enoneYield 83%

Reagents, catalysts & solvents 1

HCID 23690538Potassium phosphate (KH5(PO4)2)Solvent

Procedure

(R)-3-(3-Benzyloxybenzyl)-4-oxocyclopent-2-enyl acetate (1.8 kg, 5.35 mol) was added to KH2PO4—H3PO4 buffer solution (20 L). The mixture was added Lipase derived from Pseudomonas cepacia and 1N NaOH was slowly added to the solution at room temperature to keep the ph=7˜7.5. After 8 hours, (R)-3-(3-Benzyloxybenzyl)-4-oxocycl opent-2-enyl acetate remained about 10%, The reaction mixture was filtered to remove Lipase and the filtrate was extracted with EtOAc, dried over MgSO4, and evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent to give the (R)-4-hydroxy-2-(3-benzyloxybenzyl)cyclopent-2-enone as yellow oil: 1.3 kg (yield: 83%, >99% ee by HPLC using a chiral column)

Workup

  1. additionThe mixture was added Lipase
  2. additionwas slowly added to the solution at room temperature
  3. filtrationThe reaction mixture was filtered
  4. customto remove Lipase
  5. extractionthe filtrate was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe resulting residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-0fc6d7a88086431f91364095d38e1986
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

Loading…