Lithium Hydroxide → 5-(3-Benzyloxy-phenyl)-3-cyclopentyl-3-hydroxy-pentanoic acid

HRID 356533Notes

Reaction equation

HRID 356533 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][C:8]([CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)([OH:25])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=1)(C)(C)C.[OH-].[Li+]>CO.O>[CH2:18]([O:17][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][C:8]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)([OH:25])[CH2:7][C:6]([OH:31])=[O:5])[CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 53999177Tert-butyl 5-[3-(benzyloxy)phenyl]-3-cyclopentyl-3-hydroxypentanoate

Product 1

HCID 187986415-(3-Benzyloxy-phenyl)-3-cyclopentyl-3-hydroxy-pentanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The title compound was prepared by dissolving (S) 5-(3-benzyloxy-phenyl)-3-cyclopentyl-3-hydroxy-pentanoic acid tert-butyl ester (1.6 g, 3.8 mmol) from Example CCCCC in methanol (20 mL). Lithium hydroxide (0.32 g, 7.6 mmol) in H2O (5 mL) was added and the reaction heated to reflux overnight, cooled and pumped to dryness under vacuum. The product was partitioned between H2O and Et2O. The aqueous layer was decanted, acidified with 1N HCl and extracted with EtOAc. The organic phase was dried (MgSO4), and concentrated to give the title compound. 1H-NMR (CDCl3) δ 1.3-1.7 (m, 8 H), 1.85-1.95 (m, 2 H), 2.3 (t, 1 H), 2.45-2.7 (m, 4 H), 5.1 (s, 2 H), 6.75-6.85 (m, 3 H), 7.15 (t, 1 H), 7.3-7.45 (m, 5 H).

Workup

  1. customThe title compound was prepared
  2. temperaturethe reaction heated
  3. temperatureto reflux overnight
  4. temperaturecooled
  5. customThe product was partitioned between H2O and Et2O
  6. customThe aqueous layer was decanted
  7. extractionextracted with EtOAc
  8. dry with materialThe organic phase was dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-54ee194c3e9449f3aa90cce1282979f6
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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