Hydrochloric Acid → 1-(4-Benzyloxy-benzenesulfonyl)-5-hydroxy-piperidine-2-carboxylic acid

HRID 2269316Notes

Reaction equation

HRID 2269316 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]3[CH2:24][CH2:25][CH:19]2[C:20](=[O:26])[O:21]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:30]CC1.Cl.[Li+].[OH-]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]([OH:21])[CH2:24][CH2:25][CH:19]2[C:20]([OH:30])=[O:26])(=[O:16])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 183337695-(4-Benzyloxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one

Product 1

HCID 181794331-(4-Benzyloxy-benzenesulfonyl)-5-hydroxy-piperidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-(4-benzyloxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (0.10 g, 0.26 mmol) and 2 mL of THF was added 0.2 mL of 1M aqueous HCl. After stirring for 10 min, 0.15 mL of 12M aqueous HCL was added. After stirring for 30 min, TLC indicated no detectable reaction. The mixture was then treated with 2 mL of saturated aqueous LiOH and 2 mL of methanol. After stirring for 20 min at room temperature, the mixture was acidified with 1M HCl, extracted 3× into ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo, affording 1-(4-benzyloxy-benzenesulfonyl)-5-hydroxy-piperidine-2-carboxylic acid (0.10 g) as a colorless syrup:

Workup

  1. addition0.15 mL of 12M aqueous HCL was added
  2. stirringAfter stirring for 30 min
  3. customno detectable reaction
  4. stirringAfter stirring for 20 min at room temperature
  5. extractionextracted 3× into ethyl acetate
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e632d52bf5d64c1797d42385c7ddce13
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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