HCID 131721085, compound → HCID 131721084, compound

HRID 343270Notes

Reaction equation

HRID 343270 reaction equation
[O:1]=[C:2]1[CH:7]2[CH:5]3[CH:6]2[CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:3]1[CH2:4]3>P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH-].[Na+]>[O:1]=[C:2]1[CH:7]2[CH:5]3[CH:6]2[C@@H:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@H:3]1[CH2:4]3

Participants

4

Reactant 1

HCID 131721085HCID 131721085, compound

Product 1

HCID 131721084HCID 131721084, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 62657Potassium Phosphate, TribasicSolvent

Procedure

2.0 g (0.011 mol) of ethyl rac-2-oxotricyclo[2.2.1.03,5 ]heptane-7-carboxylate (compound of the formula I where R1 =Et) are stirred in 25 ml of 0.1M potassium phosphate buffer, pH=7, at 50° C. with 300 mg of lipase SP 526 from Candida antarctica (Novo Nordisk) using a magnetic stirrer. The pH is kept constant with the aid of an autotitrator. After metering in approximately 12.0 ml of 0.5M NaOH, the reaction mixture is extracted with tert-butyl methyl ether. After drying with Na2SO4 and concentrating the organic phase, 0.89 g (0.005 mol, 90%) of ethyl (1R,7R)-(+)-2-oxotricyclo[2.2.1.03,5 ]heptane-7-carboxylate (HPLC [Chiracel OD, n-hexane+EtOH:100+1.1 ml/min, 210 nm]; 98% ee) is obtained.

Workup

  1. customat 50° C.
  2. extractionthe reaction mixture is extracted with tert-butyl methyl ether
  3. dry with materialAfter drying with Na2SO4
  4. concentrationconcentrating the organic phase

Sources & evidence

ORD record
ord-03f0219c631f412981a68256964c24e1
Source dataset
uspto-grants-1999_01
Patent number
US05861304

Reaction notes

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