Water → HCID 178525745, compound

HRID 969551Notes

Reaction equation

HRID 969551 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1.O>CC(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C@H:12]2[CH2:13][CH2:14][C@H:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 962WaterHCID 178472385HCID 178472385, compound

Product 1

HCID 178525745HCID 178525745, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

trans Ethyl 4-[4-(3,4-dichlorophenoxy)-1-piperidinyl]-cyclohexanecarboxylate (0.8 g) was dissolved in t-BuOH (180 ml) at 38° C. To this was added Candia rugosa lipase powder (3 g). This was stirred for 30 minutes then water (20 ml) was added over 4 h. The mixture was then stirred for 48 h and filtered. The enzyme was washed with 9:1 t-BuOH-water (2×20 ml) and the filtrate was evaporated. Ethyl acetate was added to the residue and then decanted. The resultant solid was dissolved in methanol/DMSO and was purified by HPLC (Waters XTerra® column with at-column dilution of sample) (gradient (5% MeCN/NH3(aq) (0.2%) to 40% MeCN//NH3(aq) (0.2%)] gave the title compound (0.44 g) as a white solid.

Workup

  1. stirringThe mixture was then stirred for 48 h
  2. filtrationfiltered
  3. washThe enzyme was washed with 9:1 t-BuOH-water (2×20 ml)
  4. customthe filtrate was evaporated
  5. additionEthyl acetate was added to the residue
  6. customdecanted
  7. dissolutionThe resultant solid was dissolved in methanol/DMSO
  8. customwas purified by HPLC (Waters XTerra® column with at-column dilution of sample) (gradient (5% MeCN/NH3(aq) (0.2%) to 40% MeCN//NH3(aq) (0.2%)]

Sources & evidence

ORD record
ord-086e541647ab4c00ac92a0620e39a1d4
Source dataset
uspto-grants-2007_12
Patent number
US07307090B2

Reaction notes

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