Sodium Hydroxide → {2-Hydroxy-7,7-dimethyl-1-[(spiro[indene-1,4'-piperidine]-1'-sulfonyl)methyl]bicyclo[2.2.1]heptan-2-yl}acetic acid

HRID 1534800Notes

Reaction equation

HRID 1534800 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][C:6]1([OH:33])[CH2:11][CH:10]2[C:12]([CH3:14])([CH3:13])[C:7]1([CH2:15][S:16]([N:19]1[CH2:24][CH2:23][C:22]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25]3)[CH2:21][CH2:20]1)(=[O:18])=[O:17])[CH2:8][CH2:9]2)C.[OH-].[Na+]>CO.O>[OH:33][C:6]1([CH2:5][C:4]([OH:34])=[O:3])[CH2:11][CH:10]2[C:12]([CH3:13])([CH3:14])[C:7]1([CH2:15][S:16]([N:19]1[CH2:20][CH2:21][C:22]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25]3)[CH2:23][CH2:24]1)(=[O:17])=[O:18])[CH2:8][CH2:9]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 76480054HCID 76480054, compound

Product 1

HCID 3083288{2-Hydroxy-7,7-dimethyl-1-[(spiro[indene-1,4'-piperidine]-1'-sulfonyl)methyl]bicyclo[2.2.1]heptan-2-yl}acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(1S(1.Alpha.,2α,4.alpha))-2-hydroxy-7,7-dimethyl-1-((spiro(1H-indene-1,4'-piperidin)-1'-yl sulfonyl)methyl)bicyclo(2.2.1)heptane-2-acetic acid ethyl ester (3.8 g, 7.8 mmol) was stirred in methanol (40 ml) containing sodium hydroxide (10 ml of a 1.0M solution in water; 10 mmol) for 4.5 hrs. The mixture was evaporated to dryness in vacuo, treated with water (250 ml) and washed with ether. The aqueous layer was acidified with conc HCl and extracted with ether, and the ether layer from this extraction was dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed an a silica gel column eluted with CH2Cl2 followed by 90:10:0.1:0.1 of CH2Cl2 :MeOH:HOAc:H2O. The product fractions were evaporated to dryness in vacuo, and the residue was triturated with ether and hexane and filtered to give the title compound as a solid: (mp 137.5°-139.5°).

Workup

  1. customThe mixture was evaporated to dryness in vacuo
  2. additiontreated with water (250 ml)
  3. washwashed with ether
  4. extractionextracted with ether
  5. extractionthe ether layer from this extraction
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe residue was chromatographed an a silica gel column
  10. washeluted with CH2Cl2
  11. customThe product fractions were evaporated to dryness in vacuo
  12. customthe residue was triturated with ether and hexane
  13. filtrationfiltered

Sources & evidence

ORD record
ord-f10694bfdaa6499b84e717a5ca612458
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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